Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof

ABSTRACT

Five-membered heteroaromatic keratin dyeing compounds with one, two, or three heteroatoms. This invention further relates to a composition for the oxidative dyeing of keratin fibers, comprising a medium suitable for dyeing and one or more 5-membered heteroaromatic keratin dyeing compounds with one, tow, or three heteroatoms. This invention further relates to a method for oxidative dyeing of keratin fibers, comprising applying such compositions in the presence of an oxidizing agent, for a period sufficient to develop the desired coloration.

CROSS REFERENCE TO RELATED APPLICATION(S)

This application claims the benefit of provisional application Ser. No.60/541,113, filed Feb. 2, 2003.

FIELD OF INVENTION

This invention relates to 5-membered heteroaromatic keratin dyeingcompounds with one, two, or three heteroatoms, compositions for theoxidative dyeing of keratin fibers (preferably hair) comprising suchcompounds, and use thereof.

BACKGROUND OF THE INVENTION

The most extensively used method currently employed to color hair is byan oxidative process that utilizes one or more oxidative hair coloringagents in combination with one or more oxidizing agents.

Commonly, a peroxy oxidizing agent is used in combination with one ormore developers or couplers, generally small molecules capable ofdiffusing into hair. In this procedure, a peroxide material, such ashydrogen peroxide, activates the developers so that they react with thecouplers to form larger sized compounds in the hair shaft to give avariety of shades and colors.

A wide variety of developers and couplers have been employed in suchoxidative hair coloring systems and compositions. However, there stillexists a need for additional keratin dyeing compounds that can act asboth developers and couplers that safely provide color benefits.

SUMMARY OF THE INVENTION

This invention relates to 5-membered heteroaromatic keratin dyeingcompounds with one, two, or three heteroatoms according to the formulasdefined herein. This invention also relates to a composition for theoxidative dyeing of keratin fibers, comprising a medium suitable fordyeing and one or more 5-membered heteroaromatic keratin dyeingcompounds with one, tow, or three heteroatoms. This invention furtherrelates to a method for oxidative dyeing of keratin fibers, comprisingapplying such compositions in the presence of an oxidizing agent, for aperiod sufficient to develop the desired coloration. The keratin dyeingcompounds of the present invention can act as both a developer and acoupler.

It is to be understood that within the scope of this invention, numerouspotentially and actually tautomeric compounds are involved. Thus, forexample, 2-mercaptopyridine (I) exists under known conditions in thepyridine-2-thione tautomer form (II). It is to be understood that whenthis development refers to a particular structure, all of the reasonableadditional tautomeric structures are included. In the art, tautomericstructures are frequently represented by one single structure and thepresent invention follows this general practice.

DETAILED DESCRIPTION OF THE INVENTION

While the specification concludes with claims that particularly pointout and distinctly claim the invention, it is believed the presentinvention will be better understood from the following description.

The present invention relates to 5-membered heteroaromatic keratindyeing compounds with one, two, or three heteroatoms. The compounds ofthe present invention can act as both developers and/or couplers thatsafely provide color benefits.

Herein, “comprising” means that other steps and other ingredients whichdo not affect the end result can be added. This term encompasses theterms “consisting of” and “consisting essentially of”. Thecompounds/compositions and methods/processes of the present inventioncan comprise, consist of, and consist essentially of the essentialelements and limitations of the invention described herein, as well asany of the additional or optional ingredients, components, steps, orlimitations described herein.

All percentages, parts and ratios are based upon the total weight of thecompositions of the present invention, unless otherwise specified. Allsuch weights as they pertain to listed ingredients are based on theactive level and, therefore, do not include solvents or by-products thatmay be included in commercially available materials, unless otherwisespecified. The term “weight percent” may be denoted as “wt. %” herein.

Except as otherwise noted, all amounts including part, percentages, andproportions are understood to be modified by the word “about”, andamounts are not intended to indicate significant digits. Except asotherwise noted, the articles “a”, “an”, and “the” mean “one or more”.

As used herein, the term “keratin” refers to a scleroprotein found inepidermal tissues and modified into hard structures such as horns, hair,and nails. Thus, “keratinous fibers” refers to those found in hair, skinand nails and various animal body parts such as horns, hooves andfeathers.

As used herein, the term “hair” refers to keratinous fibers on a living,e.g. a person, or non-living body, e.g. in a wig, hairpiece, or otheraggregation of non-living keratinous fibers. Mammalian, preferablyhuman, hair is a preferred. Notably, hair, wool, fur, and otherkeratinous fibers are suitable substrates for coloring by the compoundsand compositions described herein.

As used herein, the term “keratin dyeing compounds” refers to compoundsthat may be used in the composition to act as developers, couplers, orboth, in order to provide color to ketatinous fibers.

As used herein, the term “keratin dyeing composition” refers to thecomposition containing one or more keratin dyeing compounds, includingthe compounds described herein.

As used herein, “cosmetically acceptable” means that ingredients whichthe term describes are suitable for use in contact with the skin or hairof humans and lower animals without undue toxicity, incompatibility,instability, irritation, allergic response, and the like.

I. Keratin Dyeing Compounds

The inventive compounds are 5-membered heteroaromatic keratin dyeingcompounds with one, two, or three heteroatoms relating to the followingcompounds:

wherein Z is selected from the group consisting of S and O;

wherein Y is selected from the group consisting of NA¹, S and O;

wherein R¹, R², R³, and R⁴ are the same or different and are selectedfrom the group consisting of

-   -   (a) C-linked monovalent substituents selected from the group        consisting of:        -   (i) substituted or unsubstituted, straight or branched,            alkyl, mono- or poly-unsaturated alkyl, heteroalkyl,            aliphatic, heteroaliphatic, or heteroolefinic systems,        -   (ii) substituted or unsubstituted, mono- or poly-cyclic            aliphatic, aryl, or heterocyclic systems, and        -   (iii) substituted or unsubstituted, mono-, poly-, or            per-fluoro alkyl systems; wherein said systems of (i), (ii)            and (iii) comprise from about 1 to about 10 carbon atoms and            from about 0 to about 5 heteroatoms selected from the group            consisting of O, S, N, P, and Si;        -   wherein substituents of the substituted systems of the            C-linked monovalent substituents are selected from the group            consisting of amino, hydroxyl, alkylamino (linear, branched,            or cyclic C1-C5), dialkylamino (linear, branched, or cyclic            C1-C5), hydroxyalkylamino (linear, branched, or cyclic            C1-C5), dihydroxyalkylamino (linear, branched, or cyclic            C1-C5), arylamino or substituted arylamino (substituents are            halogen, C1-C5 alkyl, C1-C5 alkoxy, trifluoromethyl, amino,            C1-C5 alkylamino), heteroarylamino or substituted            heteroarylamino (substituents are halogen, C1-C5 alkyl,            C1-C5 alkoxy, trifluoromethyl, amino, C1-C5 alkylamino),            arylmethylamino or substituted arylmethylamino (substituents            are halogen, C1-C5 alkyl, C1-C5 alkoxy, trifluoromethyl,            amino, C1-C5 alkylamino), and heteroarylmethylamino or            substituted heteroarylmethylamino (substituents are halogen,            C1-C5 alkyl, C1-C5 alkoxy, trifluoromethyl, amino, C1-C5            alkylamino),    -   (b) S-linked monovalent substituents selected from the group        consisting of SA¹, SO₂A¹, SO₃A¹, SSA¹, SOA¹, SO₂NA¹A², SNA¹A²,        and SONA¹A²;    -   (c) O-linked monovalent substituents selected from the group        consisting of OA¹, and ONA¹A²;    -   (d) N-linked monovalent substituents selected from the group        consisting of NA¹A², (NA¹A²A³)⁺, NA¹OA², NA¹SA², NO₂, N═NA¹,        N═NOA¹, and NA¹CN, NA¹NA²A³;    -   (e) monovalent substituents selected from the group consisting        of COOA¹, CONA¹ ₂, CONA¹COA², C(═NA¹)NA¹A², CN, and X;    -   (f) fluoroalkyl monovalent substituents selected from the group        consisting of mono-, poly-, and per-fluoro alkyl systems        comprising from about 1 to about 12 carbon atoms and from about        0 to about 4 heteroatoms; and    -   (g) hydrogen,

wherein A¹, A², and A³ are monovalent and are independently selectedfrom the group consisting of: H; substituted or unsubstituted, straightor branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl,aliphatic, heteroaliphatic, or heteroolefinic systems; substituted orunsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclicsystems; and substituted or unsubstituted, mono-, poly-, or per-fluoroalkyl systems, or A¹ and A² together with nitrogen atoms to which theyare bound form a ring; wherein said systems comprise from about 1 toabout 10 carbon atoms and from about 0 to about 5 heteroatoms selectedfrom the group consisting of O, S, N, P, and Si;

wherein X is a halogen selected from the group consisting of F, Cl, Br,and I.

In a preferred embodiment, R¹, R¹, R³, and R⁴ are selected from thegroup consisting of a hydrogen atom; a halogen atom such as chlorine,bromine or fluorine; an amino substituent, a hydroxyl substituent; acyano substituent; a C₁-C₄ alkyl substituent; a trifluoromethylsubstituent, an alkylamino substituent (e.g., N,N-dimethylamino,N,N-diethylamino, N-methylamino, or N-ethylamino); a hydroxyalkylaminosubstituent (e.g., N-(hydroxyethyl)amino, N-hydroxymethylamino,N-hydroxypropylamino, N,N-bis(hydroxyethyl)amino,N-(2,3-dihydroxypropyl)amino or N,N-bis(hydroxypropyl)amino); anacetylamido substituent; a carboxyl substituent or its esters; an alkoxysubstituent (e.g., methoxy, ethoxy, propyloxy, benzyloxy, methoxyethoxy,phenoxyethoxy, 2-cyanoethoxy, phenethyloxy, phenoxyethoxy,p-chlorobenzyloxy or methoxyethylcarbamoylmethoxy); an alkoxyalkylsubstituent (e.g., methoxymethyl, methoxyethyl, methoxypropyl,ethoxymethyl, ethoxyethyl or ethoxypropyl); a carbamoyl substituent; analkylcarbamoyl substituent (e.g., methylcarbamoyl, ethylcarbamoyl,dimethylcarbamoyl, or diethylcarbamoyl); a hydroxyalkylcarbamoylsubstituent (e.g., 2-hydroxyethylcarbamoyl,bis(2-hydroxyethyl)carbamoyl, hydroxymethylcarbamoyl,bis(hydroxymethyl)carbamoyl); an amido substituent; an alkylamidosubstituent (e.g., acetamido, propionamido, or butyramido); analkylcarbonyl substituent (e.g., acetyl, butyryl, or propionyl), analkoxycarbonyl substituent (e.g., methoxycarbonyl, ethoxycarbonyl, orpropoxycarbonyl); an aryloxy substituent (e.g., phenoxy,4-methoxyphenoxy, 4-nitrophenoxy, 4-cyanophenoxy,4-methanesulfonamidophenoxy, 4-methanesulfonylphenoxy, 3-methylphenoxyor 1-naphthyloxy); an acyloxy substituent (e.g., acetoxy, propanoyloxy,benzolyloxy, 2,4-dichlorobenzolyloxy, ethoxyalkyloxy, pyruviloyloxy,cinnamoyloxy or myristoyloxy); an alkylthio substituent (e.g.,methylthio, ethylthio, propylthio, butylthio, 2-cyanoethylthio,benzylthio, phenethylthio, 2-(diethylamino)ethylthio, ethoxyethylthio orphenoxyethylthio); an arylthio substituent (e.g., phenylthio,4-carboxyphenylthio, 2-ethoxy-5-tert-butylphenylthio,2-carboxyphenylthio or 4-methanesulfonylphenylthio); a heteroarylthiosubstituent (e.g., 5-phenyl-2,3,4,5-tetrazolyloxy or2-benzothiazolyloxy); a heteroaryloxy substituent (e.g.,5-phenyl-2,3,4,5-tetrazolyloxy or 2-benzothiazolyloxy); a 3-, 4-, 5-,6-, or 7-membered heterocycle having at least one nitrogen, oxygen orsulfur atom (e.g., pyridyl, quinolyl, morpholyl, furyl, tetrahydrofuryl,pyrazolyl, triazolyl, tetrazolyl, oxazolyl, imidazolyl, thiadiazolyl,pyrollidine, piperidine, morpholine, piperazine, indoline,hexahydroazepine, aziridine, and azetidine) and being optionallysubstituted; an aryl substituent (e.g., phenyl or naphthyl) which isoptionally substituted; a sulfonyl substituent; a sulfinyl substituent;a phosphonyl substituent; a sulfamoyl substituent; a siloxy substituent;an acyloxy substituent; a carbamoyloxy substituent; a sulphonamidesubstituent; an imide substituent; a ureido substituent; asulfamoylamino substituent; an alkoxycarbonylamino substituent; anaryloxycarbonylamino substituent; an aryloxycarbonyl substituent; and abenzenesulfonamido substituent.

If the compound of the present invention is utilized as a developer,preferred R1, R2, or R4 substituents are selected from the groupsconsisting of Amino, hydroxyl, a 3-, 4-, 5-, 6-, or 7-memberedheterocycle having at least one nitrogen, oxygen or sulfur atom (e.g.,pyridyl, quinolyl, morpholyl, furyl, tetrahydrofuryl, pyrazolyl,triazolyl, tetrazolyl, oxazolyl, imidazolyl, thiadiazolyl, pyrollidine,piperidine, morpholine, piperazine, indoline, hexahydroazepine,aziridine, and azetidine) and being optionally substituted, Alkylamino(linear, branched, or cyclic C1-C5), Dialkylamino (linear, branched, orcyclic C1-C5), Hydroxyalkylamino (linear, branched, or cyclic C1-C5),Dihydroxyalkylamino (linear, branched, or cyclic C1-C5), Arylamino orsubstituted arylamino (substituents are halogen, C1-C5 alkyl, C1-C5alkoxy, trifluoromethyl, amino, C1-C5 alkylamino), Heteroarylamino orsubstituted heteroarylamino (substituents are halogen, C1-C5 alkyl,C1-C5 alkoxy, trifluoromethyl, amino, C1-C5 alkylamino), Arylmethylaminoor substituted arylmethylamino (substituents are halogen, C1-C5 alkyl,C1-C5 alkoxy, trifluoromethyl, amino, C1-C5 alkylamino), andHeteroarylmethylamino or substituted heteroarylmethylamino (substituentsare halogen, C1-C5 alkyl, C1-C5 alkoxy, trifluoromethyl, amino, C1-C5alkylamino).

If the compound of the present invention is utilized as a coupler,preferred substituents are selected from the group consisting of Amino,Hydroxyl, Alkylamino (linear, branched, or cyclic C1-C5),Hydroxyalkylamino (linear, branched, or cyclic C1-C5), Arylamino orsubstituted arylamino (substituents are halogen, C1-C5 alkyl, C1-C5alkoxy, trifluoromethyl, amino, C1-C5 alkylamino), Heteroarylamino orsubstituted heteroarylamino (substituents are halogen, C1-C5 alkyl,C1-C5 alkoxy, trifluoromethyl, amino, C1-C5 alkylamino), Arylmethylaminoor substituted arylmethylamino (substituents are halogen, C1-C5 alkyl,C1-C5 alkoxy, trifluoromethyl, amino, C1-C5 alkylamino), andHeteroarylmethylamino or substituted heteroarylmethylamino (substituentsare halogen, C1-C5 alkyl, C1-C5 alkoxy, trifluoromethyl, amino, C1-C5alkylamino).

The developers and couplers of the present invention can alsoaccommodate nucleofugic leaving groups selected from the groupconsisting of hydrogen, chlorine, cyano, alkoxy, phenoxy,methylsulfonyoxy, pyridone and pyridazone.

In a preferred embodiment, the couplers of the present invention areutilized in compositions together with suitable 5-membered ringdevelopers chosen from the following classes: thiophenes, pyrroles,furans, pyrazoles, imidazoles, thiazoles, oxazoles, isothiazoles, orisoxazoles. In a more preferred embodiment, the couplers of the presentinvention are utilized in compositions together with pyrazoles. In aneven more preferred embodiment, the couplers of the present inventionare utilized in compositions together with the following pyrazoles:1-methyl-1H-pyrazole-4,5-diamine,2-(4,5-diamino-1H-pyrazol-1-yl)ethanol,1-isopropyl-1H-pyrazole-4,5-diamine,1-(4-methylbenzyl)-1H-pyrazole-4,5-diamine,1-(benzyl)-1H-pyrazole-4,5-diamine,1-(4-chlorobenzyl)-1H-pyrazole-4,5-diamine and1-Hydroxyethyl-4,5-diaminopyrazole sulphate. Even more preferably, thecouplers of the present invention are utilized in compositions togetherwith 1-methyl-1H-pyrazole-4,5-diamine;1-Hydroxyethyl-4,5-diaminopyrazole sulphate; and2-(4,5-diamino-1H-pyrazol-1-yl)ethanol. While not being bound to theory,such combinations enable the achievement of desired more hypsochromiccolors (e.g., yellow) relative to conventional combinations ofdevelopers and couplers.

Preferred developers and couplers include the following compounds withone, two, or three heteroatoms:

A. 5-Membered Rings with One Heteroatom

Five membered rings with one heteroatom include thiophenes, pyrroles,furans, and substitutions thereof.

1. Thiophenes

a. Preferred Developers

Preferred developers are selected from the group consisting ofThiophene-2,5-diamine; N-Methyl-thiophene-2,5-diamine;N-Ethyl-thiophene-2,5-diamine; N-Propyl-thiophene-2,5-diamine;2-(5-Amino-thiophen-2-ylamino)-ethanol;3-(5-Amino-thiophen-2-ylamino)-propan-1-ol;3-(5-Amino-thiophen-2-ylamino)-propane-1,2-diol;N-Phenyl-thiophene-2,5-diamine; N-Benzyl-thiophene-2,5-diamine;N-Thiophen-2-ylmethyl-thiophene-2,5-diamine;N-Furan-2-ylmethyl-thiophene-2,5-diamine;3-Methyl-thiophene-2,5-diamine; 3,N′5′-Dimethyl-thiophene-2,5-diamine;N′5′-Ethyl-3-methyl-thiophene-2,5-diamine;3-Methyl-N′5′-propyl-thiophene-2,5-diamine;2-(5-Amino-4-methyl-thiophen-2-ylamino)-ethanol;3-(5-Amino-4-methyl-thiophen-2-ylamino)-propan-1-ol;3-(5-Amino-4-methyl-thiophen-2-ylamino)-propane-1,2-diol;3,4-Dimethyl-thiophene-2,5-diamine;3,4,N-Trimethyl-thiophene-2,5-diamine;N-Ethyl-3,4-dimethyl-thiophene-2,5-diamine;3,4-Dimethyl-N-propyl-thiophene-2,5-diamine;2-(5-Amino-3,4-dimethyl-thiophen-2-ylamino)-ethanol;3-(5-Amino-3,4-dimethyl-thiophen-2-ylamino)-propan-1-ol;3-(5Amino-3,4-dimethyl-thiophen-2-ylamino)-propane-1,2-diol;N,N-Dimethyl-thiophene-2,5-diamine; N,N-Diethyl-thiophene-2,5-diamine;N-Ethyl-N-methyl-thiophene-2,5-diamine;5-Pyrrolidin-1-yl-thiophen-2-ylamine;2-[(5-Amino-thiophen-2-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(5-Amino-thiophen-2-yl)-methyl-amino]-ethanol;2-[(5-Amino-thiophen-2-yl)-ethyl-amino]-ethanol;3-Methoxy-thiophene-2,5-diamine; 3-Ethoxy-thiophene-2,5-diamine;3-Phenoxy-thiophene-2,5-diamine; 3-Benzyloxy-thiophene-2,5-diamine;3-Fluoro-thiophene-2,5-diamine; 3-Chloro-thiophene-2,5-diamine;2,5-Diamino-thiophene-3-carbonitrile; 3-Phenyl-thiophene-2,5-diamine;[2,3′]Bithiophenyl-2′,5′-diamine; 3-Furan-2-yl-thiophene-2,5-diamine;Thiophene-2,3-diamine; 4-Methyl-thiophene-2,3-diamine;4,5-Dimethyl-thiophene-2,3-diamine;4-Methoxy-5-methyl-thiophene-2,3-diamine;4-Chloro-thiophene-2,3-diamine; 5-Phenyl-thiophene-2,3-diamine;4-Phenyl-thiophene-2,3-diamine; 4-Thiazol-2-yl-thiophene-2,3-diamine;5-Furan-2-yl-thiophene-2,3-diamine; 5-(pyrrolidin-1-yl)thiophen-2-amine;5-Furan-2-yl-thiophene-2,3-diamine; and 5-amino-thiophen-2-ol.

Especially preferred developers of the present invention are selectedfrom the group consisting of thiophene-2,5-diamine;5-(pyrrolidin-1-yl)thiophen-2-amine;2,5-diamino-thiophene-3-carbonitrile; thiophene-2,3-diamine;4-methylthiophene-2,3-diamine; N-Methyl-thiophene-2,5-diamine; and3-Methyl-thiophene-2,5-diamine.

b. Preferred Couplers

Preferred couplers are selected from the group consisting ofThiophen-2-amine, 5-methylthiophene-2-amine, 4-methylthiophen-2-amine,4-Methoxy-thiophen-2-amine, Thiophene-3,4-diamine,4-Amino-thiophen-3-ol, thiophene-2,4-diamine, 3-methoxythiophene,2-methoxythiophene, 2-aminothiophene-3-carboxylic acid,2,3-dihydrothieno[3,4-b][1,4]dioxine, thiophen-2-ol, thiophen-3-ol,thiophen-2,3-diol, thiophen-2,4-diol, thiophen-2,5-diol,thiophen-3,4-diol, 2-aminothiophen-3-ol, 2-aminothiophen-4-ol,2-aminothiophen-5-ol, 3-aminothiophen-2-ol, 3-aminothiophen-4-ol,3-aminothiophen-5-ol, 4-aminothiophen-2-ol, 4-aminothiophen-5-ol,5-aminothiophen-4-ol, 2-methoxythiophen-3-amine,2-methoxythiophen-4-amine, 2-methoxythiophen-5-amine,3-methoxythiophen-2-amine, 3-methoxythiophen-4-amine,3-methoxythiophen-5-amine, 4-methoxythiophen-2-amine,2-methoxythiophen-3-ol, 2-methoxythiophen-4-ol, 2-methoxythiophen-5-ol,3-methoxythiophen-2-ol, 3-methoxythiophen-4-ol, 3-methoxythiophen-5-ol,4-methoxythiophen-2-ol, 2,5-dimethoxythiophene, 2,3-dimethoxythiophene,2,4-dimethoxythiophene, 3-methylthiophen-2-amine,2-methylthiophen-3-amine, 4-methylthiophen-3-amine,5-methylthiophen-3-amine, 2-cyanothiophen-3,4-diamine,2-cyanothiophen-3,5-diamine, 3-cyanothiophen-2-amine,3-cyanothiophen-5-amine, 3-cyanothiophen-2,4-diamine,3-cyanothiophen-2,5-diol, 2-cyanothiophen-3,4-diol,2-cyanothiophen-3,5-diol, 3-cyanothiophen-2-ol, 3-cyanothiophen-4-ol,3-cyanothiophen-5-ol, 3-cyanothiophen-2,4-diol,3-chlorothiophen-2,5-diamine, 3,4-chlorothiophen-2,5-diamine,2-chlorothiophen-3-amine, 2-chlorothiophen-4-amine,2-chlorothiophen-5-amine, 2-chlorothiophen-3,4-diamine,2-chlorothiophen-3,5-diamine, 3-chlorothiophen-2-amine,3-chlorothiophen-4-amine, 3-chlorothiophen-5-amine,3-chlorothiophen-2,4-diamine, 3-chlorothiophen-2,5-diol,2-chlorothiophen-3-ol, 2-chlorothiophen-4-ol, 2-chlorothiophen-5-ol,2-chlorothiophen-3,4-diol, 2-chlorothiophen-3,5-diol,3-chlorothiophen-2-ol, 3-chlorothiophen-4-ol, 3-chlorothiophen-5-ol,3-chlorothiophen-2,4-diol, 5-aminothiophen-2-carboxylic acid,3-aminothiophen-2-carboxylic acid, 4-aminothiophen-2-carboxylic acid,3,4-diaminothiophen-2-carboxylic acid, 3,5-diaminothiophen-2-carboxylicacid, 4,5-diaminothiophen-2-carboxylic acid,2-aminothiophen-3-carboxylic acid, 4-aminothiophen-3-carboxylic acid,5-aminothiophen-3-carboxylic acid, 2,4-diaminothiophen-3-carboxylicacid, 2,5-diaminothiophen-3-carboxylic acid,4,5-diaminothiophen-3-carboxylic acid, 5-hydroxythiophen-2-carboxylicacid, 3-hydroxythiophen-2-carboxylic acid,4-hydroxythiophen-2-carboxylic acid, 3,4-dihydroxythiophen-2-carboxylicacid, 3,5-dihydroxythiophen-2-carboxylic acid,4,5-dihydroxythiophen-2-carboxylic acid, 2-hydroxythiophen-3-carboxylicacid, 4-hydroxythiophen-3-carboxylic acid,5-hydroxythiophen-3-carboxylic acid, 2,4-dihydroxythiophen-3-carboxylicacid, 2,5-dihydroxythiophen-3-carboxylic acid,4,5-dihydroxythiophen-3-carboxylic acid, 5-methoxythiophen-2-carboxylicacid, 3-methoxythiophen-2-carboxylic acid,4-methoxythiophen-2-carboxylic acid, 3,4-dimethoxythiophen-2-carboxylicacid, 3,5-dimethoxythiophen-2-carboxylic acid,4,5-dimethoxythiophen-2-carboxylic acid, 2-methoxythiophen-3-carboxylicacid, 4-methoxythiophen-3-carboxylic acid,5-methoxythiophen-3-carboxylic acid, 2,4-dimethoxythiophen-3-carboxylicacid, 2,5-dimethoxythiophen-3-carboxylic acid,4,5-dimethoxythiophen-3-carboxylic acid; 2,5-dimethylthiophene,2-methylthiophene, 2,3-dimethylthiophene, 3,4-dimethylthiophene,2,4-dimethylthiophene, thiophene-3-amine, and 5-methyl-thiophen-2-amine.

Especially preferred couplers of the present invention are selected fromthe group consisting of thiophene-2-amine; 5-methylthiophene-2-amine;4-methylthiophen-2-amine; thiophene-3,4-diamine; 4-aminothiophen-3-ol;thiophene-2,4-diamine; 3-methoxythiophene; 2-methoxythiophene;2-aminothiophene-3-carboxylic acid;2,3-dihydrothieno[3,4-b][1,4]dioxine; 2,5-dimethylthiophene;2-methylthiophene; 3,4-dimethylthiophene; 2,4-dimethylthiophene;thiophen-2-ol; thiophen-2,4-diol; thiophen-2,5-diol;5-methyl-thiophen-2-amine; and thiophene-3-amine.

2. Pyrroles

a. Preferred Developers

Preferred developers are selected from the group consisting of1H-Pyrrole-2,5-diamine; N-Ethyl-1H-pyrrole-2,5-diamine;N-Propyl-1H-pyrrole-2,5-diamine;2-(5-Amino-1H-pyrrol-2-ylamino)-ethanol;3-(5-Amino-1H-pyrrol-2-ylamino)-propan-1-ol;3-(5-Amino-1H-pyrrol-2-ylamino)-propane-1,2-diol;1-Methyl-1H-pyrrole-2,5-diamine; 1,N-Dimethyl-1H-pyrrole-2,5-diamine;N-Ethyl-1-methyl-1H-pyrrole-2,5-diamine;1-Methyl-N-propyl-1H-pyrrole-2,5-diamine;2-(5-Amino-1-methyl-1H-pyrrol-2-ylamino)-ethanol;3-(5-Amino-1-methyl-1H-pyrrol-2-ylamino)-propan-1-ol;3-(5-Amino-1-methyl-1H-pyrrol-2-ylamino)-propane-1,2-diol;1-Benzyl-1H-pyrrole-2,5-diamine;1-Benzyl-N-methyl-1H-pyrrole-2,5-diamine;1-Benzyl-N-ethyl-1H-pyrrole-2,5-diamine;1-Benzyl-N-propyl-1H-pyrrole-2,5-diamine;2-(5-Amino-1-benzyl-1H-pyrrol-2-ylamino)-ethanol;3-(5-Amino-1-benzyl-1H-pyrrol-2-ylamino)-propan-1-ol;3-(5-Amino-1-benzyl-1H-pyrrol-2-ylamino)-propane-1,2-diol;1-Isopropyl-1H-pyrrole-2,5-diamine;1-Isopropyl-N-methyl-1H-pyrrole-2,5-diamine;N-Ethyl-1-isopropyl-1H-pyrrole-2,5-diamine;1-Isopropyl-N-propyl-1H-pyrrole-2,5-diamine;2-(5-Amino-1-isopropyl-1H-pyrrol-2-ylamino)-ethanol;3-(5-Amino-1-isopropyl-1H-pyrrol-2-ylamino)-propan-1-ol;3-(5-Amino-1-isopropyl-1H-pyrrol-2-ylamino)-propane-1,2-diol;N,N-Dimethyl-1H-pyrrole-2,5-diamine; N,N-Diethyl-1H-pyrrole-2,5-diamine;N-Ethyl-N-methyl-1H-pyrrole-2,5-diamine;2,3,4,5-Tetrahydro-1′H-[1,2′]bipyrrolyl-5′-ylamine;2-[(5-Amino-1H-pyrrol-2-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(5-Amino-1H-pyrrol-2-yl)-methyl-amino]-ethanol;2-[(5-Amino-1H-pyrrol-2-yl)-ethyl-amino]-ethanol;1,N,N-Trimethyl-1H-pyrrole-2,5-diamine;N,N-Diethyl-1-methyl-1H-pyrrole-2,5-diamine;N-Ethyl-1,N-dimethyl-1H-pyrrole-2,5-diamine;1′-Methyl-2,3,4,5-tetrahydro-1′H-[1,2′]bipyrrolyl-5′-ylamine;2-[(5-Amino-1-methyl-1H-pyrrol-2-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(5-Amino-1-methyl-1H-pyrrol-2-yl)-methyl-amino]-ethanol;2-[(5-Amino-1-methyl-1H-pyrrol-2-yl)-ethyl-amino]-ethanol;1-Benzyl-N,N-dimethyl-1H-pyrrole-2,5-diamine;1-Benzyl-N,N-diethyl-1H-pyrrole-2,5-diamine;1-Benzyl-N-ethyl-N-methyl-1H-pyrrole-2,5-diamine;1′-Benzyl-2,3,4,5-tetrahydro-1′H-[1,2′]bipyrrolyl-5′-ylamine;2-[(5-Amino-1-benzyl-1H-pyrrol-2-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(5-Amino-1-benzyl-1H-pyrrol-2-yl)-methyl-amino]-ethanol;2-[(5-Amino-1-benzyl-1H-pyrrol-2-yl)-ethyl-amino]-ethanol;2-[(5-Amino-1-benzyl-1H-pyrrol-2-yl)-ethyl-amino]-ethanol;3-Methoxy-1H-pyrrole-2,5-diamine; 3-Ethoxy-1H-pyrrole-2,5-diamine;3-Phenoxy-1H-pyrrole-2,5-diamine; 3-Phenoxy-1H-pyrrole-2,5-diamine;3-Benzyloxy-1H-pyrrole-2,5-diamine; 3-Fluoro-1H-pyrrole-2,5-diamine;3-Chloro-1H-pyrrole-2,5-diamine; 2,5-Diamino-1H-pyrrole-3-carbonitrile;3-Phenyl-1H-pyrrole-2,5-diamine; 3-Thiophen-2-yl-1H-pyrrole-2,5-diamine;3-Furan-2-yl-1H-pyrrole-2,5-diamine;3-Methoxy-1-methyl-1H-pyrrole-2,5-diamine;3-Ethoxy-1-methyl-1H-pyrrole-2,5-diamine;1-Methyl-3-phenoxy-1H-pyrrole-2,5-diamine;3-Benzyloxy-1-methyl-1H-pyrrole-2,5-diamine;3-Fluoro-1-methyl-1H-pyrrole-2,5-diamine;3-Chloro-1-methyl-1H-pyrrole-2,5-diamine;2,5-Diamino-1-methyl-1H-pyrrole-3-carbonitrile;1-Methyl-3-phenyl-1H-pyrrole-2,5-diamine;1-Methyl-3-thiophen-2-yl-1H-pyrrole-2,5-diamine; and3-Furan-2-yl-1-methyl-1H-pyrrole-2,5-diamine;2,5-diamino-pyrrole-3-carbonitrile; pyrrole-2,3-diamine;4-methylpyrrole-2,3-diamine; N-Methyl-pyrrole-2,5-diamine;3-Methyl-pyrrole-2,5-diamine; and 5-amino-1-methyl-1H-pyrrol-2-ol.

Especially preferred developers of the present invention are selectedfrom the group consisting of 1-methyl-1H-pyrrole-2,5-diamine;2,3,4,5-tetrahydro-1″H[1,2′]bipyrrolyl-5′-ylamine;2-(5-Amino-1H-pyrrol-2-ylamino)-ethanol; 1H-Pyrrole-2,5-diamine;2,5-diamino-pyrrole-3-carbonitrile; pyrrole-2,3-diamine;4-methylpyrrole-2,3-diamine; N-Methyl-pyrrole-2,5-diamine; and3-Methyl-pyrrole-2,5-diamine.

b. Preferred Couplers

Preferred couplers are selected from the group consisting of1-Methyl-1H-pyrrole-3,4-diamine, 4-Amino-1-methyl-1H-pyrrol-3-ol,1-Benzyl-1H-pyrrole-3,4-diamine, 4-amino-1H-pyrrole-3-carboxylic acid,1H-pyrrole-2-amine, 5-methyl-1H-pyrrole-2-amine,4-methyl-1H-pyrrole-2-amine, 4-Methoxy-1H-pyrrole-2-amine,1H-pyrrole-3,4-diamine, 4-Amino-1H-pyrrole-3-ol, 1H-pyrrole-2,4-diamine,3-methoxy-1H-pyrrole, 2-methoxy-1H-pyrrole,2-amino-1H-pyrrole-3-carboxylic acid,2,3-dihydrothieno[3,4-b][1,4]dioxine, 1H-pyrrole-2-ol, 1H-pyrrole-3-ol,1H-pyrrole-2,3-diol, 1H-pyrrole-2,4-diol, 1H-pyrrole-2,5-diol,1H-pyrrole-3,4-diol, 2-amino-1H-pyrrole-3-ol, 2-amino-1H-pyrrole-4-ol,2-amino-1H-pyrrole-5-ol, 3-amino-1H-pyrrole-2-ol,4-amino-1H-pyrrole-2-ol, 4-amino-1H-pyrrole-5-ol,5-amino-1H-pyrrole-4-ol, 2-methoxy-1H-pyrrole-3-amine,2-methoxy-1H-pyrrole-4-amine, 2-methoxy-1H-pyrrole-5-amine,3-methoxy-1H-pyrrole-2-amine, 3-methoxy-1H-pyrrole-4-amine,4-methoxy-1H-pyrrole-2-amine, 2-methoxy-1H-pyrrole-3-ol,2-methoxy-1H-pyrrole-4-ol, 2-methoxy-1H-pyrrole-5-ol,3-methoxy-1H-pyrrole-2-ol, 3-methoxy-1H-pyrrole-4-ol,4-methoxy-1H-pyrrole-2-ol, 2,5-dimethoxy-1H-pyrrole,2,3-dimethoxy-1H-pyrrole, 2,4-dimethoxy-1H-pyrrole,4-methyl-1H-pyrrole-3-amine, 5-methyl-1H-pyrrole-3-amine,2-cyano-1H-pyrrole-4-amine, 2-cyano-1H-pyrrole-5-amine,2-cyano-1H-pyrrole-3,4-diamine, 2-cyano-1H-pyrrole-3,5-diamine,3-cyano-1H-pyrrole-2-amine, 3-cyano-1H-pyrrole-4-amine,3-cyano-1H-pyrrole-5-amine, 3-cyano-1H-pyrrole-2,4-diamine,3-cyano-1H-pyrrole-2,5-diol, 2-cyano-1H-pyrrole-3-ol,2-cyano-1H-pyrrole-4-ol, 2-cyano-1H-pyrrole-5-ol,2-cyano-1H-pyrrole-3,4-diol, 2-cyano-1H-pyrrole-3,5-diol,3-cyano-1H-pyrrole-2-ol, 3-cyano-1H-pyrrole-4-ol,3-cyano-1H-pyrrole-5-ol, 3-cyano-1H-pyrrole-2,4-diol,3-chloro-1H-pyrrole-2,5-diamine, 3,4-chloro-1H-pyrrole-2,5-diamine,2-chloro-1H-pyrrole-3-amine, 2-chloro-1H-pyrrole-4-amine,2-chloro-1H-pyrrole-5-amine, 2-chloro-1H-pyrrole-3,4-diamine,2-chloro-1H-pyrrole-3,5-diamine, 3-chloro-1H-pyrrole-2-amine,3-chloro-1H-pyrrole-4-amine, 3-chloro-1H-pyrrole-5-amine,3-chloro-1H-pyrrole-2,4-diamine, 3-chloro-1H-pyrrole-2,5-diol,2-chloro-1H-pyrrole-3-ol, 2-chloro-1H-pyrrole-4-ol,2-chloro-1H-pyrrole-5-ol, 2-chloro-1H-pyrrole-3,4-diol,2-chloro-1H-pyrrole-3,5-diol, 3-chloro-1H-pyrrole-2-ol,3-chloro-1H-pyrrole-4-ol, 3-chloro-1H-pyrrole-5-ol,3-chloro-1H-pyrrole-2,4-diol, 5-amino-1H-pyrrole-2-carboxylic acid,3-amino-1H-pyrrole-2-carboxylic acid, 4-amino-1H-pyrrole-2-carboxylicacid, 3,4-diamino-1H-pyrrole-2-carboxylic acid,3,5-diamino-1H-pyrrole-2-carboxylic acid,4,5-diamino-1H-pyrrole-2-carboxylic acid,2-amino-1H-pyrrole-3-carboxylic acid, 4-amino-1H-pyrrole-3-carboxylicacid, 5-amino-1H-pyrrole-3-carboxylic acid,2,4-diamino-1H-pyrrole-3-carboxylic acid,2,5-diamino-1H-pyrrole-3-carboxylic acid,4,5-diamino-1H-pyrrole-3-carboxylic acid,5-hydroxy-1H-pyrrole-2-carboxylic acid,3-hydroxy-1H-pyrrole-2-carboxylic acid,4-hydroxy-1H-pyrrole-2-carboxylic acid,3,4-dihydroxy-1H-pyrrole-2-carboxylic acid,3,5-dihydroxy-1H-pyrrole-2-carboxylic acid,4,5-dihydroxy-1H-pyrrole-2-carboxylic acid,2-hydroxy-1H-pyrrole-3-carboxylic acid,4-hydroxy-1H-pyrrole-3-carboxylic acid,5-hydroxy-1H-pyrrole-3-carboxylic acid,2,4-dihydroxy-1H-pyrrole-3-carboxylic acid,2,5-dihydroxy-1H-pyrrole-3-carboxylic acid,4,5-dihydroxy-1H-pyrrole-3-carboxylic acid,5-methoxy-1H-pyrrole-2-carboxylic acid,3-methoxy-1H-pyrrole-2-carboxylic acid,4-methoxy-1H-pyrrole-2-carboxylic acid,3,4-dimethoxy-1H-pyrrole-2-carboxylic acid,3,5-dimethoxy-1H-pyrrole-2-carboxylic acid,4,5-dimethoxy-1H-pyrrole-2-carboxylic acid,2-methoxy-1H-pyrrole-3-carboxylic acid,4-methoxy-1H-pyrrole-3-carboxylic acid,5-methoxy-1H-pyrrole-3-carboxylic acid,2,4-dimethoxy-1H-pyrrole-3-carboxylic acid,2,5-dimethoxy-1H-pyrrole-3-carboxylic acid,4,5-dimethoxy-1H-pyrrole-3-carboxylic acid,4-amino-1-methyl-1H-pyrrole-3-carboxylic acid, 1H-pyrrole-2-amine,1,5-dimethyl-1H-pyrrole-2-amine, 1,4-dimethyl-2-amine,4-Methoxy-1-methyl-1H-pyrrole-2-amine, 1H-pyrrole-3,4-diamine,4-Amino-1-methyl-1H-pyrrole-3-ol, 1-methyl-1H-pyrrole-2,4-diamine,3-methoxy-1-methyl-1H-pyrrole, 2-methoxy-1-methyl-1H-pyrrole,2-amino-1-methyl-1H-pyrrole-3-carboxylic acid,2-amino-1-methyl-1H-pyrrole-4-ol, 2-amino-1-methyl-1H-pyrrole-5-ol,3-amino-1-methyl-1H-pyrrole-2-ol, 3-amino-1-methyl-1H-pyrrole-4-ol,3-amino-1-methyl-1H-pyrrole-5-ol, 4-amino-1-methyl-1H-pyrrole-2-ol,4-amino-1-methyl-1H-pyrrole-3-ol, 4-amino-1-methyl-1H-pyrrole-5-ol,5-amino-1-methyl-1H-pyrrole-3-ol, 5-amino-1-methyl-1H-pyrrole-4-ol,2-methoxy-1-methyl-1H-pyrrole-3-amine,2-methoxy-1-methyl-1H-pyrrole-4-amine,2-methoxy-1-methyl-1H-pyrrole-5-amine,3-methoxy-1-methyl-1H-pyrrole-2-amine,3-methoxy-1-methyl-1H-pyrrole-4-amine,3-methoxy-1-methyl-1H-pyrrole-5-amine,4-methoxy-1-methyl-1H-pyrrole-2-amine,2-methoxy-1-methyl-1H-pyrrole-3-ol, 2-methoxy-1-methyl-1H-pyrrole-4-ol,2-methoxy-1-methyl-1H-pyrrole-5-ol, 3-methoxy-1-methyl-1H-pyrrole-2-ol,3-methoxy-1-methyl-1H-pyrrole-4-ol, 3-methoxy-1-methyl-1H-pyrrole-5-ol,4-methoxy-1-methyl-1H-pyrrole-2-ol, 2,5-dimethoxy-1-methyl-1H-pyrrole,2,3-dimethoxy-1-methyl-1H-pyrrole, 2,4-dimethoxy-1-methyl-1H-pyrrole,1,3-dimethyl-1H-pyrrole-2-amine, 1,2-dimethyl-1H-pyrrole-3-amine,1,4-dimethyl-1H-pyrrole-3-amine, 1,5-dimethyl-1H-pyrrole-3-amine,3-cyano-1-methyl-1H-pyrrole-2,5-diamine,2-cyano-1-methyl-1H-pyrrole-3-amine,2-cyano-1-methyl-1H-pyrrole-4-amine,2-cyano-1-methyl-1H-pyrrole-5-amine,2-cyano-1-methyl-1H-pyrrole-3,4-diamine,2-cyano-1-methyl-1H-pyrrole-3,5-diamine,3-cyano-1-methyl-1H-pyrrole-2-amine,3-cyano-1-methyl-1H-pyrrole-4-amine,3-cyano-1-methyl-1H-pyrrole-5-amine,3-cyano-1-methyl-1H-pyrrole-2,4-diamine,3-cyano-1-methyl-1H-pyrrole-2,5-diol, 2-cyano-1-methyl-1H-pyrrole-3-ol,2-cyano-1-methyl-1H-pyrrole-4-ol, 2-cyano-1-methyl-1H-pyrrole-5-ol,2-cyano-1-methyl-1H-pyrrole-3,4-diol,2-cyano-1-methyl-1H-pyrrole-3,5-diol, 3-cyano-1-methyl-1H-pyrrole-2-ol,3-cyano-1-methyl-1H-pyrrole-4-ol, 3-cyano-1-methyl-1H-pyrrole-5-ol,3-cyano-1-methyl-1H-pyrrole-2,4-diol,3-chloro-1-methyl-1H-pyrrole-2,5-diamine,2-chloro-1-methyl-1H-pyrrole-3-amine,2-chloro-1-methyl-1H-pyrrole-4-amine,2-chloro-1-methyl-1H-pyrrole-5-amine,2-chloro-1-methyl-1H-pyrrole-3,4-diamine,2-chloro-1-methyl-1H-pyrrole-3,5-diamine,3-chloro-1-methyl-1H-pyrrole-2-amine,3-chloro-1-methyl-1H-pyrrole-4-amine,3-chloro-1-methyl-1H-pyrrole-5-amine,3-chloro-1-methyl-1H-pyrrole-2,4-diamine,3-chloro-1-methyl-1H-pyrrole-2,5-diol,3,4-chloro-1-methyl-1H-pyrrole-2,5-diol,2-chloro-1-methyl-1H-pyrrole-3-ol, 2-chloro-1-methyl-1H-pyrrole-4-ol,2-chloro-1-methyl-1H-pyrrole-5-ol,2-chloro-1-methyl-1H-pyrrole-3,4-diol,2-chloro-1-methyl-1H-pyrrole-3,5-diol,3-chloro-1-methyl-1H-pyrrole-2-ol, 3-chloro-1-methyl-1H-pyrrole-4-ol,3-chloro-1-methyl-1H-pyrrole-5-ol,3-chloro-1-methyl-1H-pyrrole-2,4-diol,5-amino-1-methyl-1H-pyrrole-2-carboxylic acid,3-amino-1-methyl-1H-pyrrole-2-carboxylic acid,4-amino-1-methyl-1H-pyrrole-2-carboxylic acid,3,4-diamino-1-methyl-1H-pyrrole-2-carboxylic acid,3,5-diamino-1-methyl-1H-pyrrole-2-carboxylic acid,4,5-diamino-1-methyl-1H-pyrrole-2-carboxylic acid,2-amino-1-methyl-1H-pyrrole-3-carboxylic acid,4-amino-1-methyl-1H-pyrrole-3-carboxylic acid,5-amino-1-methyl-1H-pyrrole-3-carboxylic acid,2,4-diamino-1-methyl-1H-pyrrole-3-carboxylic acid,2,5-diamino-1-methyl-1H-pyrrole-3-carboxylic acid,4,5-diamino-1-methyl-1H-pyrrole-3-carboxylic acid,5-hydroxy-1-methyl-1H-pyrrole-2-carboxylic acid,3-hydroxy-1-methyl-1H-pyrrole-2-carboxylic acid,4-hydroxy-1-methyl-1H-pyrrole-2-carboxylic acid,3,4-dihydroxy-1-methyl-1H-pyrrole-2-carboxylic acid,3,5-dihydroxy-1-methyl-1H-pyrrole-2-carboxylic acid,4,5-dihydroxy-1-methyl-1H-pyrrole-2-carboxylic acid,2-hydroxy-1-methyl-1H-pyrrole-3-carboxylic acid,4-hydroxy-1-methyl-1H-pyrrole-3-carboxylic acid,5-hydroxy-1-methyl-1H-pyrrole-3-carboxylic acid,2,4-dihydroxy-1-methyl-1H-pyrrole-3-carboxylic acid,2,5-dihydroxy-1-methyl-1H-pyrrole-3-carboxylic acid,4,5-dihydroxy-1-methyl-1H-pyrrole-3-carboxylic acid,5-methoxy-1-methyl-1H-pyrrole-2-carboxylic acid,3-methoxy-1-methyl-1H-pyrrole-2-carboxylic acid,4-methoxy-1-methyl-1H-pyrrole-2-carboxylic acid,3,4-dimethoxy-1-methyl-1H-pyrrole-2-carboxylic acid,3,5-dimethoxy-1-methyl-1H-pyrrole-2-carboxylic acid,4,5-dimethoxy-1-methyl-1H-pyrrole-2-carboxylic acid,2-methoxy-1-methyl-1H-pyrrole-3-carboxylic acid,4-methoxy-1-methyl-1H-pyrrole-3-carboxylic acid,5-methoxy-1-methyl-1H-pyrrole-3-carboxylic acid,2,4-dimethoxy-1-methyl-1H-pyrrole-3-carboxylic acid,2,5-dimethoxy-1-methyl-1H-pyrrole-3-carboxylic acid,4,5-dimethoxy-1-methyl-1H-pyrrole-3-carboxylic acid,2,5-dimethylpyrrole, 2-methylpyrrole, 2,3-dimethylpyrrole,3,4-dimethylpyrrole, 2,4-dimethylpyrrole, and 2-ethylpyrrole.

Especially preferred couplers are selected from the group consisting of1H-pyrrol-2-amine; 1-methyl-1H-pyrrole-3,4-diamine;4-amino-1-methyl-1H-pyrrol-3-ol; 4-amino-1H-pyrrole-3-carboxylic acid;2,5-dimethylpyrrole; 2-methylpyrrole; 3,4-dimethylpyrrole;2,4-dimethylpyrrole; 1H-pyrrole-3,4-diamine; 1H-pyrrole-2,4-diamine;1H-pyrrole-2-ol; 1H-pyrrole; 1H-pyrrole-2,5-diol; and 2-ethylpyrrole.

3. Furans

a. Preferred Developers

Preferred developers are selected from the group consisting ofFuran-2,5-diamine; N-Methyl-furan-2,5-diamine;N-Ethyl-furan-2,5-diamine; N-Propyl-furan-2,5-diamine;2-(5-Amino-furan-2-ylamino)-ethanol;3-(5-Amino-furan-2-ylamino)-propan-1-ol;3-(5-Amino-furan-2-ylamino)-propane-1,2-diol;N,N-Dimethyl-furan-2,5-diamine; N,N-Diethyl-furan-2,5-diamine;N-Ethyl-N-methyl-furan-2,5-diamine; 5-Pyrrolidin-1-yl-furan-2-ylamine;2-[(5-Amino-furan-2-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(5-Amino-furan-2-yl)-methyl-amino]-ethanol;2-[(5-Amino-furan-2-yl)-ethyl-amino]-ethanol;3-Fluoro-furan-2,5-diamine; 3-Chloro-furan-2,5-diamine;3-Trifluoromethyl-furan-2,5-diamine;5-Amino-2-methylamino-furan-3-carbonitrile;2,5-Diamino-furan-3-carbonitrile;5-Amino-2-ethylamino-furan-3-carbonitrile;5-Amino-2-propylamino-furan-3-carbonitrile;5-Amino-2-(2-hydroxy-ethylamino)-furan-3-carbonitrile;5-Amino-2-(3-hydroxy-propylamino)-furan-3-carbonitrile;5-Amino-2-(2,3-dihydroxy-propylamino)-furan-3-carbonitrile;5-Amino-2-dimethylamino-furan-3-carbonitrile;5-Amino-2-diethylamino-furan-3-carbonitrile;5-Amino-2-(ethyl-methyl-amino)-furan-3-carbonitrile;5-Amino-2-pyrrolidin-1-yl-furan-3-carbonitrile;5-Amino-2-[bis-(2-hydroxy-ethyl)-amino]-furan-3-carbonitrile;5-Amino-2-[(2-hydroxy-ethyl)-methyl-amino]-furan-3-carbonitrile;5-Amino-2-[ethyl-(2-hydroxy-ethyl)-amino]-furan-3-carbonitrile; and5-amino-furan-2-ol.

Especially preferred developers of the present invention are selectedfrom the group consisting of furan-2,5-diamine;2-(5-Amino-1H-furan-2-ylamino)-ethanol;2,5-diamino-furan-3-carbonitrile; furan-2,3-diamine;4-methylfuran-2,3-diamine; and 3-Methyl-furan-2,5-diamine.

b. Preferred Couplers

Preferred couplers are selected from the group consisting offuran-3,4-diamine, 4-amino-furan-3-ol, 4-aminofuran-3-carboxylic acid,furan-2-amine, 5-methylfuran-2-amine, 4-methylfuran-2-amine,4-methoxyfuran-2-amine, furan-2,4-diamine, 3-methoxyfuran,2-methoxyfuran, 2-aminofuran-3-carboxylic acid, furan-2-ol, furan-3-ol,furan-2,3-diol, furan-2,4-diol, furan-2,5-diol, furan-3,4-diol,2-aminofuran-3-ol, 2-aminofuran-4-ol, 2-aminofuran-5-ol,3-aminofuran-2-ol, 3-aminofuran-4-ol, 4-aminofuran-2-ol,4-aminofuran-5-ol, 5-aminofuran-4-ol, 2-methoxyfuran-3-amine,2-methoxyfuran-4-amine, 2-methoxyfuran-5-amine, 3-methoxyfuran-2-amine,3-methoxyfuran-4-amine, 3-methoxyfuran-5-amine, 4-methoxyfuran-2-amine,2-methoxyfuran-3-ol, 2-methoxyfuran-4-ol, 2-methoxyfuran-5-ol,3-methoxyfuran-2-ol, 3-methoxyfuran-4-ol, 3-methoxyfuran-5-ol,4-methoxyfuran-2-ol, 2,5-dimethoxyfuran, 2,3-dimethoxyfuran,2,4-dimethoxyfuran, 3-methylfuran-2-amine, 2-methylfuran-3-amine,4-methylfuran-3-amine, 5-methylfuran-3-amine, 3-cyanofuran-2,5-diamine,2-cyanofuran-3-amine, 2-cyanofuran-4-amine, 2-cyanofuran-5-amine,2-cyanofuran-3,4-diamine, 2-cyanofuran-3,5-diamine,3-cyanofuran-2-amine, 3-cyanofuran-4-amine, 3-cyanofuran-5-amine,3-cyanofuran-2,4-diamine, 3-cyanofuran-2,5-diol, 2-cyanofuran-3-ol,2-cyanofuran-4-ol, 2-cyanofuran-5-ol, 2-cyanofuran-3,4-diol,2-cyanofuran-3,5-diol, 3-cyanofuran-2-ol, 3-cyanofuran-4-ol,3-cyanofuran-5-ol, 3-cyanofuran-2,4-diol, 3-chlorofuran-2,5-diamine,2-chlorofuran-3-amine, 2-chlorofuran-4-amine, 2-chlorofuran-5-amine,2-chlorofuran-3,4-diamine, 2-chlorofuran-3,5-diamine,3-chlorofuran-2-amine, 3-chlorofuran-4-amine, 3-chlorofuran-5-amine,3-chlorofuran-2,4-diamine, 3-chlorofuran-2,5-diol, 2-chlorofuran-3-ol,2-chlorofuran-4-ol, 2-chlorofuran-5-ol, 2-chlorofuran-3,4-diol,2-chlorofuran-3,5-diol, 3-chlorofuran-2-ol, 3-chlorofuran-4-ol,3-chlorofuran-5-ol, 3-chlorofuran-2,4-diol, 5-aminofuran-2-carboxylicacid, 3-aminofuran-2-carboxylic acid, 4-aminofuran-2-carboxylic acid,3,4-diaminofuran-2-carboxylic acid, 3,5-diaminofuran-2-carboxylic acid,4,5-diaminofuran-2-carboxylic acid, 2-aminofuran-3-carboxylic acid,4-aminofuran-3-carboxylic acid, 5-aminofuran-3-carboxylic acid,2,4-diaminofuran-3-carboxylic acid, 2,5-diaminofuran-3-carboxylic acid,4,5-diaminofuran-3-carboxylic acid, 5-hydroxyfuran-2-carboxylic acid,3-hydroxyfuran-2-carboxylic acid, 4-hydroxyfuran-2-carboxylic acid,3,4-dihydroxyfuran-2-carboxylic acid, 3,5-dihydroxyfuran-2-carboxylicacid, 4,5-dihydroxyfuran-2-carboxylic acid, 2-hydroxyfuran-3-carboxylicacid, 4-hydroxyfuran-3-carboxylic acid, 5-hydroxyfuran-3-carboxylicacid, 2,4-dihydroxyfuran-3-carboxylic acid,2,5-dihydroxyfuran-3-carboxylic acid, 4,5-dihydroxyfuran-3-carboxylicacid, 5-methoxyfuran-2-carboxylic acid, 3-methoxyfuran-2-carboxylicacid, 4-methoxyfuran-2-carboxylic acid, 3,4-dimethoxyfuran-2-carboxylicacid, 3,5-dimethoxyfuran-2-carboxylic acid,4,5-dimethoxyfuran-2-carboxylic acid, 2-methoxyfuran-3-carboxylic acid,4-methoxyfuran-3-carboxylic acid, 5-methoxyfuran-3-carboxylic acid,2,4-dimethoxyfuran-3-carboxylic acid, 2,5-dimethoxyfuran-3-carboxylicacid, 4,5-dimethoxyfuran-3-carboxylic acid, 2,5-dimethylfuran,2-methylfuran, 2,3-dimethylfuran, 3,4-dimethylfuran, 2,4-dimethylfuran,furan-3-methanol, 5-methyl-furan-2-ol, and (furan-2-yl)methanol.

Especially preferred couplers of the present invention are selected fromthe group consisting of furan-2-amine; furan-3,4-diamine;4-amino-furan-3-ol; 4-amino-furan-3-carboxylic acid; 2,5-dimethylfuran;2-methylfuran; 3,4-dimethylfuran; 2,4-dimethylfuran; 2-methoxyfuran;furan-3-methanol; 5-methyl-furan-2-ol; and (furan-2-yl)methanol.

B. 5-Membered Rings with Two Heteroatoms

Five membered rings with two heteroatoms include thiazoles, oxazoles,isothiazoles, isoxazoles, imidazoles, and substitutions thereof.

1. Thiazoles

a. Preferred Developers

Preferred developers are selected from the group consisting ofThiazole-2,5-diamine; N′2′-Methyl-thiazole-2,5-diamine;N′2′-Ethyl-thiazole-2,5-diamine; N′2′-Propyl-thiazole-2,5-diamine;2-(5-Amino-thiazol-2-ylamino)-ethanol;3-(5-Amino-thiazol-2-ylamino)-propan-1-ol;3-(5-Amino-thiazol-2-ylamino)-propane-1,2-diol;N′2′,N′2′-Dimethyl-thiazole-2,5-diamine;N′2′,N′2′-Diethyl-thiazole-2,5-diamine;N′2′-Ethyl-N′2′-methyl-thiazole-2,5-diamine;N′2′-Ethyl-N′2′-propyl-thiazole-2,5-diamine;2-[(5-Amino-thiazol-2-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(5-Amino-thiazol-2-yl)-methyl-amino]-ethanol;2-[(5-Amino-thiazol-2-yl)-ethyl-amino]-ethanol;N′5′-Methyl-thiazole-2,5-diamine; N′5′-Ethyl-thiazole-2,5-diamine;N′5′-Propyl-thiazole-2,5-diamine; 2-(2-Amino-thiazol-5-ylamino)-ethanol;3-(2-Amino-thiazol-5-ylamino)-propan-1-ol;3-(2-Amino-thiazol-5-ylamino)-propane-1,2-diol;N′5′,N′5′-Dimethyl-thiazole-2,5-diamine;N′5′,N′5′-Diethyl-thiazole-2,5-diamine;N′5′-Ethyl-N′5′-methyl-thiazole-2,5,-diamine;5-Pyrrolidin-1-yl-thiazol-2-ylamine;2-[(2-Amino-thiazol-5-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(2-Amino-thiazol-5-yl)-methyl-amino]-ethanol;2-[(2-Amino-thiazol-5-yl)-ethyl-amino]-ethanol;4-Methyl-thiazole-2,5-diamine; 4-Ethyl-thiazole-2,5-diamine;2-(2,5-Diamino-thiazol-4-yl)-ethanol; 4-Phenyl-thiazole-2,5-diamine;4-Thiophen-2-yl-thiazole-2,5-diamine; 4-Furan-2-yl-thiazole-2,5-diamine;[2,4′]Bithiazolyl-2′,5′-diamine; 4-Methoxy-thiazole-2,5-diamine;4-Ethoxy-thiazole-2,5-diamine; 4-Phenoxy-thiazole-2,5-diamine;4-Fluoro-thiazole-2,5-diamine; 4-Chloro-thiazole-2,5-diamine;4-Trifluoromethyl-thiazole-2,5-diamine; and2,5-Diamino-thiazole-4-carbonitrile; thiazole-4,5-diamine;5-aminothiazol-4-ol; 5-amino-furan-2-ol; and 2-amino-thiazol-5-ol.

Especially preferred developers of the present invention are selectedfrom the group consisting of thiazole-2,5-diamine;5-Pyrrolidin-1-yl-thiazol-2-ylamine;2-(5-Amino-thiazol-2-ylamino)-ethanol; thiazole-4,5-diamine;thiazol-2,4,5-triamine and 4-aminothiazol-5-ol.

b. Preferred Couplers

Preferred couplers are selected from the group consisting ofthiazol-5-amine, 2-methylthiazol-5-amine, 2-phenylthiazol-5-amine,thiazol-2-amine, 5-methylthiazol-2-amine, thiazol-5-ol,2-methylthiazol-5-ol, 2-phenylthiazol-5-ol, thiazol-2-ol,5-methylthiazol-2-ol, 5-phenylthiazol-2-ol, 2-aminothiazol-5-ol,2-amino-4-methylthiazol-5-ol, 2-amino-4-phenylthiazol-5-ol,2-amino-4-ethylthiazol-5-ol, 5-aminothiazol-2-ol,5-amino-4-methylthiazol-2-ol, 5-amino-4-phenylthiazol-2-ol,5-amino-4-ethylthiazol-2-ol, thiazol-2,5-diol, 4-methylthiazol-2,5-diol,4-phenylthiazol-2,5-diol, thiazol-2,5-diol, 4-methylthiazol-2,5-diol,4-phenylthiazol-2,5-diol, thiazol-2,5-diamine,4-methylthiazol-2,5-diamine, 4-phenylthiazol-2,5-diamine,5-methoxythiazole, 5-methoxy-2-methylthiazole,5-methoxy-2-phenylthiazole, 2-methoxythiazole,2-methoxy-5-methylthiazole, 2-methoxy-5-phenylthiazole,2,5-dimethoxythiazole, 2,5-dimethoxy-4-methylthiazole,2,5-dimethoxy-4-phenylthiazole, 5-aminothiazol-4-carbonitrile,5-amino-2-methylthiazol-4-carbonitrile,5-amino-2-phenylthiazol-4-carbonitrile, 5-hydroxythiazol-4-carbonitrile,5-hydroxy-2-methylthiazol-4-carbonitrile,5-hydroxy-2-phenylthiazol-4-carbonitrile,2,5-dihydroxythiazol-4-carbonitrile,2,5-dimethoxythiazol-4-carbonitrile, 4-chlorothiazol-5-ol,4-chloro-2-methylthiazol-5-ol, 4-chloro-2-phenylthiazol-5-ol,4-chlorothiazol-2,5-diol, 4-chlorothiazol-5-amine,4-chloro-2-methylthiazol-5-amine, 4-chloro-2-phenylthiazol-5-amine,4-chlorothiazol-2,5-diamine, 4-fluorothiazol-2,5-diamine,4-trifluoromethylthiazol-2,5-diamine, 2-methylthiazol-5-amine,2-methylthiazol-5-ol, thiazol-2,4-diol, 2-methylthiazol-5-amine,2-ethylthiazol-5-amine, 2-(thiazol-5-ylamino)ethanol, and3-(thiazol-5-ylamino)propane-1,2-diol.

Especially preferred couplers are selected from the group consisting ofthiazol-5-amine; 2-methyl-thiazol-5-ylamine; thiazol-2-amine;4-methylthiazol-2-amine; thiazol-2,4-diamine; thiazol-5-ol;thiazol-2,5-diol; and thiazol-2,4-diol.

2. Oxazoles

a. Preferred Developers

Preferred developers are selected from the group consisting ofOxazole-2,5-diamine; N′2′-Methyl-oxazole-2,5-diamine;N′2′-Ethyl-oxazole-2,5-diamine; N′2′-Propyl-oxazole-2,5-diamine;2-(5-Amino-oxazol-2-ylamino)-ethanol;3-(5-Amino-oxazol-2-ylamino)-propan-1-ol;3-(5-Amino-oxazol-2-ylamino)-propane-1,2-diol;N′2′-Phenyl-oxazole-2,5-diamine; N′2′-Thiophen-2-yl-oxazole-2,5-diamine;N′2′-Furan-2-yl-oxazole-2,5-diamine;N′2′-Thiazol-2-yl-oxazole-2,5-diamine; N′5′-Methyl-oxazole-2,5-diamine;N′5′-Ethyl-oxazole-2,5-diamine; N′5′-Propyl-oxazole-2,5-diamine;2-(2-Amino-oxazol-5-ylamino)-ethanol;3-(2-Amino-oxazol-5-ylamino)-propan-1-ol;3-(2-Amino-oxazol-5-ylamino)-propane-1,2-diol;N′5′-Phenyl-oxazole-2,5-diamine; N′5′-Thiophen-2-yl-oxazole-2,5-diamine;N′5′-Furan-2-yl-oxazole-2,5-diamine;N′5′-Thiazol-2-yl-oxazole-2,5-diamine; 4-Methyl-oxazole-2,5-diamine;4,N′2′-Dimethyl-oxazole-2,5-diamine;N′2′-Ethyl-4-methyl-oxazole-2,5-diamine;4-Methyl-N′2′-propyl-oxazole-2,5-diamine;2-(5-Amino-4-methyl-oxazol-2-ylamino)-ethanol;3-(5-Amino-4-methyl-oxazol-2-ylamino)-propan-1-ol;3-(5-Amino-4-methyl-oxazol-2-ylamino)-propane-1,2-diol;4-Methyl-N′2′-phenyl-oxazole-2,5-diamine;4-Methyl-N′2′-thiophen-2-yl-oxazole-2,5-diamine;N′2′-Furan-2-yl-4-methyl-oxazole-2,5-diamine;4-Methyl-N′2′-thiazol-2-yl-oxazole-2,5-diamine;4-Methyl-N′5′-thiazol-2-yl-oxazole-2,5-diamine;4-Methyl-N′5′-thiazol-2-yl-oxazole-2,5-diamine;4,N′5′-Dimethyl-oxazole-2,5-diamine;N′5′-Ethyl-4-methyl-oxazole-2,5-diamine;4-Methyl-N′5′-propyl-oxazole-2,5-diamine;2-(2-Amino-4-methyl-oxazol-5-ylamino)-ethanol;3-(2-Amino-4-methyl-oxazol-5-ylamino)-propan-1-ol;3-(2-Amino-4-methyl-oxazol-5-ylamino)-propane-1,2-diol;4-Methyl-N′5′-phenyl-oxazole-2,5-diamine;4-Methyl-N′5′-thiophen-2-yl-oxazole-2,5-diamine;N′5′-Furan-2-yl-4-methyl-oxazole-2,5-diamine;4-Phenyl-oxazole-2,5-diamine; 4-Thiophen-2-yl-oxazole-2,5-diamine;4-Furan-2-yl-oxazole-2,5-diamine; 4-Thiazol-2-yl-oxazole-2,5-diamine;4-Fluoro-oxazole-2,5-diamine; 4-Chloro-oxazole-2,5-diamine;4-Trifluoromethyl-oxazole-2,5-diamine;2,5-Diamino-oxazole-4-carbonitrile; 4-Methoxy-oxazole-2,5-diamine;4-Ethoxy-oxazole-2,5-diamine; 2-amino-thiazol-5-ol; and2-amino-oxazol-5-ol.

Especially preferred developers are selected from the group consistingof oxazol-2,5-diamine; 5-Pyrrolidin-1-yl-oxazol-2-ylamine;2-(5-Amino-oxazol-2-ylamino)-ethanol; oxazol-4,5-diamine;oxazol-2,4,5-triamine; and 4-aminooxazol-5-ol.

b. Preferred Couplers

Preferred couplers are selected from the group consisting ofoxazol-5-amine, 2-methyloxazol-5-amine, 2-phenyloxazol-5-amine,oxazol-2-amine, 5-methyl-oxazol-2-amine, oxazol-5-ol,2-methyloxazol-5-ol, 2-phenyloxazol-5-ol, oxazol-2-ol,5-methyl-oxazol-2-ol, 5-phenyloxazol-2-ol, 2-aminooxazol-5-ol,2-amino-4-methyloxazol-5-ol, 2-amino-4-phenyloxazol-5-ol,2-amino-4-ethyloxazol-5-ol, 5-aminooxazol-2-ol,5-amino-4-methyloxazol-2-ol, 5-amino-4-phenyloxazol-2-ol,5-amino-4-ethyloxazol-2-ol, oxazol-2,5-diol, 4-methyloxazol-2,5-diol,4-phenyloxazol-2,5-diol, oxazol-2,5-diol, 4-methyloxazol-2,5-diol,4-phenyloxazol-2,5-diol, oxazol-2,5-diamine, 4-methyloxazol-2,5-diamine,4-phenyloxazol-2,5-diamine, 5-methoxyoxazole, 5-methoxy-2-methyl-oxazol,5-methoxy-2-phenyl-oxazol, 2-methoxyoxazole, 2-methoxy-5-methyloxazole,2-methoxy-5-phenyloxazole, 2,5-dimethoxyoxazole,2,5-dimethoxy-4-methyloxazole, 2,5-dimethoxy-4-phenyloxazole,5-aminooxazol-4-carbonitrile, 5-amino-2-methyloxazol-4-carbonitrile,5-amino-2-phenyloxazol-4-carbonitrile, 5-hydroxyoxazol-4-carbonitrile,5-hydroxy-2-methyloxazol-4-carbonitrile,5-hydroxy-2-phenyloxazol-4-carbonitrile,2,5-dihydroxyoxazol-4-carbonitrile, 2,5-dimethoxyoxazol-4-carbonitrile,4-chlorooxazol-5-ol, 4-chloro-2-methyloxazol-5-ol,4-chloro-2-phenyloxazol-5-ol, 4-chlorooxazol-2,5-diol,4-chlorooxazol-5-amine, 4-chloro-2-methyloxazol-5-amine,4-chloro-2-phenyloxazol-5-amine, 4-chlorooxazol-2,5-diamine,4-fluorooxazol-2,5-diamine, 4-trifluoromethyloxazol-2,5-diamine,2-methyloxazol-5-amine, 2-methyloxazol-5-ol, oxazol-2,4-diol,2-methyloxazol-5-amine, 2-ethyloxazol-5-amine,2-(oxazol-5-ylamino)ethanol, and 3-(oxazol-5-ylamino)propane-1,2-diol.

Especially preferred couplers are selected from the group consisting ofoxazol-5-amine; 2-methyl-oxazol-5-amine; oxazol-2-amine;4-methyloxazol-2-amine; oxazol-2,4-diamine; oxazol-5-ol;oxazol-2,5-diol; and oxazol-2,4-diol.

3. Isothiazoles

a. Preferred Developers

Preferred developers are selected from the group consisting ofIsothiazole-4,5-diamine, 3-Methyl-isothiazole-4,5-diamine,3-Ethyl-isothiazole-4,5-diamine, 3-Propyl-isothiazole-4,5-diamine,2-(4,5-Diamino-isothiazol-3-yl)-ethanol,3-(4,5-Diamino-isothiazol-3-yl)-propan-1-ol,3-(4,5-Diamino-isothiazol-3-yl)-propane-1,2-diol,3-Furan-2-yl-isothiazole-4,5-diamine,3-Thiophen-2-yl-isothiazole-4,5-diamine,3-Phenyl-isothiazole-4,5-diamine,3-Furan-2-ylmethyl-isothiazole-4,5-diamine,3-Thiophen-2-ylmethyl-isothiazole-4,5-diamine,3-Methoxy-isothiazole-4,5-diamine, 3-Ethoxy-isothiazole-4,5-diamine,3-Phenoxy-isothiazole-4,5-diamine, 3-Benzyloxy-isothiazole-4,5-diamine,3-Fluoro-isothiazole-4,5-diamine, 3-Chloro-isothiazole-4,5-diamine,Isothiazole-3,4-diamine, 4-aminoisothiazol-5-ol,5-Methyl-isothiazole-3,4-diamine, 5-amino-isothiazol-4-ol, and4-amino-isothiazol-5-ol.

Especially preferred developers of the present invention are selectedfrom the group consisting of Isothiazole-4,5-diamine;3-methyl-isothiazole-4,5-diamine; 4-aminoisothiazol-5-ol; and3-Methoxy-isothiazole-4,5-diamine.

b. Preferred Couplers

Preferred couplers are selected from the group consisting ofisothiazol-5-amine, 3-methylisothiazol-5-amine,3-phenylisothiazol-5-amine, isothiazol-4-amine,3-methylisothiazol-5-amine, isothiazol-5-ol, 3-methylisothiazol-5-ol,3-phenylisothiazol-5-ol, isothiazol-4-ol, 5-methylisothiazol-3-ol,5-phenylisothiazol-3-ol, 3-aminoisothiazol-5-ol, 5-aminoisothiazol-3-ol,5-amino-4-chloroisothiazol-2-ol, 5-amino-4-cyanoisothiazol-2-ol,isothiazol-3,5-diol, 4-chloroisothiazol-3,5-diol,4-cyanoisothiazol-3,5-diol, 4-methoxyisothiazol-3,5-diol,4-fluoroisothiazol-3,5-diol, 4-bromoisothiazol-3,5-diol,4-ethoxyisothiazol-3,5-diol, isothiazol-3,5-diamine,4-chloroisothiazol-3,5-diamine, 4-methoxyisothiazol-3,5-diamine,4-fluoroisothiazol-3,5-diamine, 4-cyanoisothiazol-3,5-diamine,5-methoxyisothiazole, 5-methoxy-3-methylisothiazol,5-methoxy-3-phenylisothiazole, 4-methoxyisothiazole,4-methoxy-3-methylisothiazole, 4-methoxy-3-phenylisothiazole,3,5-dimethoxyisothiazole, 3,5-dimethoxy-4-chloroisothiazole,3,5-dimethoxy-4-methoxyisothiazole, 3,5-dimethoxy-4-fluoroisothiazole,3,5-dimethoxy-4-ethoxyisothiazole, 5-aminoisothiazol-4-carbonitrile,5-amino-3-methylisothiazol-4-carbonitrile,5-amino-3-phenylisothiazol-4-carbonitrile,5-hydroxyisothiazol-4-carbonitrile,5-hydroxy-3-methylisothiazol-4-carbonitrile,5-hydroxy-3-phenylisothiazol-4-carbonitrile,3,5-dihydroxyisothiazol-4-carbonitrile,3,5-dimethoxyisothiazol-4-carbonitrile, 4-chloroisothiazol-5-ol,4-chloro-3-methylisothiazol-5-ol, 4-chloro-3-phenylisothiazol-5-ol,4-chloroisothiazol-3,5-diol, 4-chloroisothiazol-5-amine,4-chloro-3-methylisothiazol-5-amine,4-chloro-3-phenylisothiazol-5-amine, 4-chloroisothiazol-3,5-diamine,4-fluoroisothiazol-3,5-diamine, 4-trifluoromethylisothiazol-3,5-diamine,3-methylisothiazol-5-amine, isothiazol-3,4-diol, isothiazol-3,4-diamine,3-methylisothiazol-5-amine, 3-ethylisothiazol-5-amine,2-(isothiazol-5-ylamino)ethanol, and3-(isothiazol-5-ylamino)propane-1,2-diol.

Especially preferred couplers of the present invention are selected fromthe group consisting of isothiazol-5-amine; 3-methylisothiazol-5-amine;3-methylisothiazol-5-amine; isothiazol-5-ol; 3-methylisothiazol-5-ol;3-aminoisothiazol-5-ol; 5-aminoisothiazol-3-ol; and isothiazol-3,5-diol.

4. Isoxazoles

a. Preferred Developers

Preferred developers are selected from the group consisting ofIsoxazole-4,5-diamine, 3-Methyl-isoxazole-4,5-diamine,3-Ethyl-isoxazole-4,5-diamine, 3-Propyl-isoxazole-4,5-diamine,2-(4,5-Diamino-isoxazol-3-yl)-ethanol,3-(4,5-Diamino-isoxazol-3-yl)-propan-1-ol,3-(4,5-Diamino-isoxazol-3-yl)-propane-1,2-diol,3-Furan-2-yl-isoxazole-4,5-diamine,3-Thiophen-2-yl-isoxazole-4,5-diamine, 3-Phenyl-isoxazole-4,5-diamine,3-Furan-2-ylmethyl-isoxazole-4,5-diamine,3-Thiophen-2-ylmethyl-isoxazole-4,5-diamine,3-Methoxy-isoxazole-4,5-diamine, 3-Ethoxy-isoxazole-4,5-diamine,3-Phenoxy-isoxazole-4,5-diamine, 3-Benzyloxy-isoxazole-4,5-diamine,3-Fluoro-isoxazole-4,5-diamine, 3-Chloro-isoxazole-4,5-diamine,Isoxazole-3,4-diamine, 5-Methyl-isoxazole-3,4-diamine,5-amino-isoxazol-4-ol, and 4-amino-isoxazol-5-ol.

Especially preferred developers of the present invention are selectedfrom the group consisting of Isoxazole-4,5-diamine;3-methyl-isoxazole-4,5-diamine; 4-aminoisoxazol-5-ol; and3-Methoxy-isoxazole-4,5-diamine.

b. Preferred Couplers

Preferred couplers are selected from the group consisting ofisoxazol-5-amine, 3-methylisoxazol-5-amine, 3-phenylisoxazol-5-amine,isoxazol-4-amine, 3-methylisoxazol-5-amine, isoxazol-5-ol,3-methylisoxazol-5-ol, 3-phenylisoxazol-5-ol, isoxazol-4-ol,5-methylisoxazol-3-ol, 5-phenylisoxazol-3-ol, 3-aminoisoxazol-5-ol,5-aminoisoxazol-3-ol, 5-amino-4-chloroisoxazol-2-ol,5-amino-4-cyanoisoxazol-2-ol, isoxazol-3,5-diol,4-chloroisoxazol-3,5-diol, 4-cyanoisoxazol-3,5-diol,4-methoxyisoxazol-3,5-diol, 4-fluoroisoxazol-3,5-diol,4-bromoisoxazol-3,5-diol, 4-ethoxyisoxazol-3,5-diol,isoxazol-3,5-diamine, 4-chloroisoxazol-3,5-diamine,4-methoxyisoxazol-3,5-diamine, 4-fluoroisoxazol-3,5-diamine,4-cyanoisoxazol-3,5-diamine, 5-methoxyisoxazole,5-methoxy-3-methylisoxazol, 5-methoxy-3-phenylisoxazole,4-methoxyisoxazole, 4-methoxy-3-methylisoxazole,4-methoxy-3-phenylisoxazole, 3,5-dimethoxyisoxazole,3,5-dimethoxy-4-chloroisoxazole, 3,5-dimethoxy-4-methoxyisoxazole,3,5-dimethoxy-4-fluoroisoxazole, 3,5-dimethoxy-4-ethoxyisoxazole,5-aminoisoxazol-4-carbonitrile, 5-amino-3-methylisoxazol-4-carbonitrile,5-amino-3-phenylisoxazol-4-carbonitrile,5-hydroxyisoxazol-4-carbonitrile,5-hydroxy-3-methylisoxazol-4-carbonitrile,5-hydroxy-3-phenylisoxazol-4-carbonitrile,3,5-dihydroxyisoxazol-4-carbonitrile,3,5-dimethoxyisoxazol-4-carbonitrile, 4-chloroisoxazol-5-ol,4-chloro-3-methylisoxazol-5-ol, 4-chloro-3-phenylisoxazol-5-ol,4-chloroisoxazol-3,5-diol, 4-chloroisoxazol-5-amine,4-chloro-3-methylisoxazol-5-amine, 4-chloro-3-phenylisoxazol-5-amine,4-chloroisoxazol-3,5-diamine, 4-fluoroisoxazol-3,5-diamine,4-trifluoromethylisoxazol-3,5-diamine, 3-methylisoxazol-5-amine,3-methylisoxazol-5-ol, isoxazol-3,4-diol, isoxazol-3,4-diamine,3-methylisoxazol-5-amine, 3-ethylisoxazol-5-amine,2-(isoxazol-5-ylamino)ethanol, and3-(isoxazol-5-ylamino)propane-1,2-diol.

Especially preferred couplers of the present invention are selected fromthe group consisting of isoxazol-5-amine; 3-methylisoxazol-5-amine;3-methylisoxazol-5-amine; isoxazol-5-ol; 3-methylisoxazol-5-ol;3-aminoisoxazol-5-ol; 5-aminoisoxazol-3-ol; and isoxazol-3,5-diol.

5. Imidazoles

a. Preferred Developers

Preferred developers are selected from the group consisting of3H-Imidazole-2,4-diamine; N′2′-Methyl-3H-imidazole-2,4-diamine;N′2′-Ethyl-3H-imidazole-2,4-diamine;N′2′-Propyl-3H-imidazole-2,4-diamine;2-(5-Amino-1H-imidazol-2-ylamino)-ethanol;3-(5-Amino-1H-imidazol-2-ylamino)-propan-1-ol;3-(5-Amino-1H-imidazol-2-ylamino)-propane-1,2-diol;N′2′-Phenyl-3H-imidazole-2,4-diamine;N′2′-Thiophen-2-yl-3H-imidazole-2,4-diamine;N′2′-Furan-2-yl-3H-imidazole-2,4-diamine;N′2′-Thiazol-2-yl-3H-imidazole-2,4-diamine;N′4′-Methyl-3H-imidazole-2,4-diamine;N′4′-Ethyl-3H-imidazole-2,4-diamine;N′4′-Propyl-3H-imidazole-2,4-diamine;2-(2-Amino-3H-imidazol-4-ylamino)-ethanol;3-(2-Amino-3H-imidazol-4-ylamino)-propan-1-ol;3-(2-Amino-3H-imidazol-4-ylamino)-propane-1,2-diol;N′4′-Phenyl-3H-imidazole-2,4-diamine;N′4′-Thiophen-2-yl-3H-imidazole-2,4-diamine;N′4′-Furan-2-yl-3H-imidazole-2,4-diamine;N′4′-Thiazol-2-yl-3H-imidazole-2,4-diamine;5-Methyl-3H-imidazole-2,4-diamine;5,N′2′-Dimethyl-3H-imidazole-2,4-diamine;N′2′-Ethyl-5-methyl-3H-imidazole-2,4-diamine;5-Methyl-N′2′-propyl-3H-imidazole-2,4-diamine;2-(5-Amino-4-methyl-1H-imidazol-2-ylamino)-ethanol;3-(5-Amino-4-methyl-1H-imidazol-2-ylamino)-propan-1-ol;3-(5-Amino-4-methyl-1H-imidazol-2-ylamino)-propane-1,2-diol;5-Methyl-N′2′-phenyl-3H-imidazole-2,4-diamine;5-Methyl-N′2′-thiophen-2-yl-3H-imidazole-2,4-diamine;N′2′-Furan-2-yl-5-methyl-3H-imidazole-2,4-diamine;5-Methyl-N′2′-thiazol-2-yl-3H-imidazole-2,4-diamine;5-Methyl-N′4′-thiazol-2-yl-3H-imidazole-2,4-diamine;5,N′4′-Dimethyl-3H-imidazole-2,4-diamine;N′4′-Ethyl-5-methyl-3H-imidazole-2,4-diamine;5-Methyl-N′4′-propyl-3H-imidazole-2,4-diamine;2-(2-Amino-5-methyl-3H-imidazol-4-ylamino)-ethanol;3-(2-Amino-5-methyl-3H-imidazol-4-ylamino)-propan-1-ol;3-(2-Amino-5-methyl-3H-imidazol-4-ylamino)-propane-1,2-diol;5-Methyl-N′4′-phenyl-3H-imidazole-2,4-diamine;5-Methyl-N′4′-thiophen-2-yl-3H-imidazole-2,4-diamine;N′4′-Furan-2-yl-5-methyl-3H-imidazole-2,4-diamine;5-Phenyl-3H-imidazole-2,4-diamine;5-Thiophen-2-yl-3H-imidazole-2,4-diamine;5-Furan-2-yl-3H-imidazole-2,4-diamine;5-Thiazol-2-yl-3H-imidazole-2,4-diamine;5-Fluoro-3H-imidazole-2,4-diamine; 5-Chloro-3H-imidazole-2,4-diamine;5-Trifluoromethyl-3H-imidazole-2,4-diamine;2,5-Diamino-1H-imidazole-4-carbonitrile;5-Methoxy-3H-imidazole-2,4-diamine; 5-Ethoxy-3H-imidazole-2,4-diamine;1H-imidazol-2,4,5-triamine; 1-methyl-1H-imidazol-2,4,5-triamine;1-phenyl-1H-imidazol-2,4,5-triamine; 4,5-diamino-1H-imidazol-2-ol;4,5-diamino-1-methyl-1H-imidazol-2-ol;4,5-diamino-1-phenyl-1H-imidazol-2-ol; 2-methyl-1H-imidazol-4,5-diamine;1,2-dimethyl-1H-imidazol-4,5-diamine;2-methyl-1-phenyl-1H-imidazol-4,5-diamine;2-methyl-4-amino-1H-imidazol-4-ol;1,2-dimethyl-4-amino-1H-imidazol-4-ol;2-methyl-4-amino-1-phenyl-1H-imidazol-4-ol;4-amino-1-methyl-1H-imidazol-2,5-diol;4-amino-1-phenyl-1H-imidazol-2,5-diol; 4-amino-1H-imidazol-2,5-diol;1H-imidazol-4,5-diamine; 1-methyl-1H-imidazol-4,5-diamine;1-phenyl-1H-imidazol-4,5-diamine; and 4-amino-isoxazol-5-ol.

Especially preferred developers of the present invention are selectedfrom the group consisting of 1H-imidazol-2,5-diamine;2-(5-Amino-1H-imidazol-2-ylamino)-ethanol; 1H-imidazol-4,5-diamine;1H-imidazol-2,4,5-triamine; and 4-amino-1H-imidazol-5-ol.

b. Preferred Couplers

Preferred couplers are selected from the group consisting of1H-imidazol-5-amine, 1-methyl-1H-imidazol-5-amine,1-phenyl-1H-imidazol-5-amine, 1H-imidazol-2-amine,1-methyl-1H-imidazol-2-amine, 1H-imidazol-5-ol,1-methyl-1H-imidazol-5-ol, 1-phenyl-1H-imidazol-5-ol, 1H-imidazol-2-ol,1-methyl-1H-imidazol-2-ol, 1-phenyl-1H-imidazol-2-ol,2-amino-1H-imidazol-5-ol, 2-amino-1-methyl-1H-imidazol-5-ol,2-amino-1-phenyl-1H-imidazol-5-ol, 2-amino-1-ethyl-1H-imidazol-5-ol,5-amino-1H-imidazol-2-ol, 5-amino-1-methyl-1H-imidazol-2-ol,5-amino-1-phenyl-1H-imidazol-2-ol, 5-amino-1-ethyl-1H-imidazol-2-ol,1H-imidazol-2,5-diol, 1-methyl-1H-imidazol-2,5-diol,1-phenyl-1H-imidazol-2,5-diol, 1H-imidazol-2,5-diol,1-methyl-1H-imidazol-2,5-diol, 1-phenyl-1H-imidazol-2,5-diol,1H-imidazol-2,5-diamine, 1-methyl-1H-imidazol-2,5-diamine,1-phenyl-1H-imidazol-2,5-diamine, 5-methoxy-1H-imidazole,5-methoxy-1-methyl-1H-imidazole, 5-methoxy-1-phenyl-1H-imidazole,2-methoxy-1H-imidazole, 2-methoxy-1-methyl-1H-imidazole,2-methoxy-1-phenyl-1H-imidazole, 2,5-dimethoxy-1H-imidazole,2,5-dimethoxy-1-methyl-1H-imidazole,2,5-dimethoxy-1-phenyl-1H-imidazole, 5-amino-1H-imidazol-4-carbonitrile,5-amino-1-methyl-1H-imidazol-4-carbonitrile,5-amino-1-phenyl-1H-imidazol-4-carbonitrile,5-hydroxy-1H-imidazol-4-carbonitrile,5-hydroxy-1-methyl-1H-imidazol-4-carbonitrile,5-hydroxy-1-phenyl-1H-imidazol-4-carbonitrile,2,5-dihydroxy-1H-imidazol-4-carbonitrile,2,5-dihydroxy-1-methyl-1H-imidazol-4-carbonitrile,2,5-dihydroxy-1-phenyl-1H-imidazol-4-carbonitrile,2,5-dimethoxy-1H-imidazol-4-carbonitrile,2,5-dimethoxy-1-methyl-1H-imidazol-4-carbonitrile,2,5-dimethoxy-1-phenyl-1H-imidazol-4-carbonitrile,4-chloro-1H-imidazol-5-ol, 4-chloro-1-methyl-1H-imidazol-5-ol,4-chloro-1-phenyl-1H-imidazol-5-ol, 4-chloro-1H-imidazol-2,5-diol,4-chloro-1-methyl-1H-imidazol-2,5-diol,4-chloro-1-phenyl-1H-imidazol-2,5-diol, 4-chloro-1H-imidazol-5-amine,4-chloro-1-methyl-1H-imidazol-5-amine,4-chloro-1-phenyl-1H-imidazol-5-amine, 4-chloro-1H-imidazol-2,5-diamine,4-chloro-1-methyl-1H-imidazol-2,5-diamine,4-chloro-1-phenyl-1H-imidazol-2,5-diamine,4-fluoro-1H-imidazol-2,5-diamine,4-fluoro-1-methyl-1H-imidazol-2,5-diamine,4-fluoro-1-phenyl-1H-imidazol-2,5-diamine,4-trifluoromethyl-1H-imidazol-2,5-diamine,1-methyl-4-trifluoromethyl-1H-imidazol-2,5-diamine,1-phenyl-4-trifluoromethyl-1H-imidazol-2,5-diamine,2-methyl-1H-imidazol-5-amine, 1,2-dimethyl-1H-imidazol-5-amine,2-methyl-1-phenyl-1H-imidazol-5-amine, 2-methyl-1H-imidazol-5-ol,1,2-dimethyl-1H-imidazol-5-ol, 2-methyl-1-phenyl-1H-imidazol-5-ol,1H-imidazol-2,4-diol, 1-methyl-1H-imidazol-2,4-diol,1-phenyl-1H-imidazol-2,4-diol, N-methyl-1H-imidazol-5-amine,N-ethyl-1H-imidazol-5-amine, 2-(1H-imidazol-5-ylamino)ethanol, and3-(1H-imidazol-5-ylamino)propane-1,2-diol.

Especially preferred couplers are selected from the group consisting of1H-imidazol-5-amine; 2-methyl-1H-imidazol-5-ylamine;1H-imidazol-2-amine; 4-methyl-1H-imidazol-2-amine;1H-imidazol-2,4-diamine; 1H-imidazol-5-ol; 1H-imidazol-2,5-diol; and1H-imidazol-2,4-diol.

C. 5-Membered Rings with Three Heteroatoms

Five membered rings with three heteroatoms include 4H-[1,2,4]triazoles,[1,3,4]thiadiazoles, [1,3,4]oxadiazoles, [1,2,5]thiadiazoles, andsubstitutions thereof.

1.4H-[1,2,4]Triazoles

a. Preferred Developers

Preferred developers are selected from the group consisting of4H-[1,2,4]Triazole-3,5-diamine; N-Methyl-4H-[1,2,4]triazole-3,5-diamine;N-Methyl-4H-[1,2,4]triazole-3,5-diamine;N-Ethyl-4H-[1,2,4]triazole-3,5-diamine;N-Propyl-4H-[1,2,4]triazole-3,5-diamine;2-(5-Amino-4H-[1,2,4]triazol-3-ylamino)-ethanol;3-(5-Amino-4H-[1,2,4]triazol-3-ylamino)-propan-1-ol;3-(5-Amino-4H-[1,2,4]triazol-3-ylamino)-propane-1,2-diol;N-Phenyl-4H-[1,2,4]triazole-3,5-diamine;N-Thiophen-2-ylmethyl-4H-[1,2,4]triazole-3,5-diamine;N-Furan-2-ylmethyl-4H-[1,2,4]triazole-3,5-diamine;N-Benzyl-4H-[1,2,4]triazole-3,5-diamine;N,N-Dimethyl-4H-[1,2,4]triazole-3,5-diamine;N,N-Diethyl-4H-[1,2,4]triazole-3,5-diamine;5-Pyrrolidin-1-yl-4H-[1,2,4]triazol-3-ylamine;2-[(5-Amino-4H-[1,2,4]triazol-3-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(5-Amino-4H-[1,2,4]triazol-3-yl)-ethyl-amino]-ethanol; and5-amino-1H-[1,2,4]triazol-3-ol.

2. [1,3,4]Thiadiazoles

a. Preferred Developers

Preferred developers are selected from the group consisting of[1,3,4]Thiadiazole-2,5-diamine; N-Methyl-[1,3,4]thiadiazole-2,5-diamine;N-Ethyl-[1,3,4]thiadiazole-2,5-diamine;N-Propyl-[1,3,4]thiadiazole-2,5-diamine;2-(5-Amino-[1,3,4]thiadiazol-2-ylamino)-ethanol;3-(5-Amino-[1,3,4]thiadiazol-2-ylamino)-propan-1-ol;3-(5-Amino-[1,3,4]thiadiazol-2-ylamino)-propane-1,2-diol;N-Phenyl-[1,3,4]thiadiazole-2,5-diamine;N-Thiophen-2-ylmethyl-[1,3,4]thiadiazole-2,5-diamine;N-Furan-2-ylmethyl-[1,3,4]thiadiazole-2,5-diamine;N-Benzyl-[1,3,4]thiadiazole-2,5-diamine;N,N-Dimethyl-[1,3,4]thiadiazole-2,5-diamine;N,N-Diethyl-[1,3,4]thiadiazole-2,5-diamine;5-Pyrrolidin-1-yl-[1,3,4]thiadiazo-2-ylamine;2-[(5-Amino-[1,3,4]thiadiazol-2-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(5-Amino-[1,3,4]thiadiazol-2-yl)-ethyl-amino]-ethanol; and5-amino-[1,3,4]thiadiazol-2-ol.

Especially preferred developers are selected from the group consistingof [1,3,4]thiadiazole-2,5-diamine;N-ethyl-[1,3,4]thiadiazole-2,5-diamine; andN-phenyl-[1,3,4]thiadiazole-2,5-diamine.

3. [1,3,4]Oxadiazoles

a. Preferred Developers

Preferred developers are selected from the group consisting of[1,3,4]Oxadiazole-2,5-diamine; N-Methyl-[1,3,4]oxadiazole-2,5-diamine;N-Ethyl-[1,3,4]oxadiazole-2,5-diamine;N-Propyl-[1,3,4]oxadiazole-2,5-diamine;2-(5-Amino-[1,3,4]oxadiazol-2-ylamino)-ethanol;3-(5-Amino-[1,3,4]oxadiazol-2-ylamino)-propan-1-ol;3-(5-Amino-[1,3,4]oxadiazol-2-ylamino)-propane-1,2-diol;N-Phenyl-[1,3,4]oxadiazole-2,5-diamine;N-Thiophen-2-ylmethyl-[1,3,4]oxadiazole-2,5-diamine;N-Furan-2-ylmethyl-[1,3,4]oxadiazole-2,5-diamine;N-Benzyl-[1,3,4]oxadiazole-2,5-diamine;N,N-Dimethyl-[1,3,4]oxadiazole-2,5-diamine;N,N-Diethyl-[1,3,4]oxadiazole-2,5-diamine;5-Pyrrolidin-1-yl-[1,3,4]oxadiazol-2-ylamine;2-[(5-Amino-[1,3,4]oxadiazol-2-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(5-Amino-[1,3,4]oxadiazol-2-yl)-ethyl-amino]-ethanol; and5-amino-[1,3,4]oxadiazol-2-ol.

4. [1,2,5]Thiadiazoles

a. Preferred Developers

Preferred developers are selected from the group consisting of[1,2,5]Thiadiazole-3,4-diamine; 4-Amino-[1,2,5]thiadiazol-3-ol;N-Methyl-[1,2,5]thiadiazole-3,4-diamine;N-Ethyl-[1,2,5]thiadiazole-3,4-diamine;2-(4-Amino-[1,2,5]thiadiazol-3-ylamino)-ethanol;2-[4-(2-Hydroxy-ethylamino)-[1,2,5]thiadiazol-3-ylamino]-ethanol; and5-amino-[1,3,4]thiadiazol-2-ol.

Especially preferred developers are selected from the group consistingof [1,2,5]thiadiazole-3,4-diamine.

D. SYNTHESIS EXAMPLES

The following are non-limiting synthesis examples of the presentinvention.

Example A Thiophene-2,5-diamine, obtainable from the following synthesisstrategy

Treatment of 5-nitro-2-thiophenecarboxylic acid 1 withdiphenylphosphoryl azide in toluene in the presence of tert-BuOH givesrise to the carbamate 2 (Tetrahedron Lett. 1999, 40, 1721). Reduction of2 with Fe/FeSO4 in MeOH results in the formation of the aminothiophene3. Reaction of 3 with trifluoroacetic acid in DCM providesthiophene-2,5-diamine 4 as its trifuoroacetic acid salt.

Example B Thiophene-2-amine, obtainable from the following synthesisstrategy

Treatment of 2-thiophenecarboxylic acid (CAS 527-72-0) withdiphenylphosphoryl azide (CAS 26386-88-9) in the presence oftert-butanol gives carbamate 2 (J. Med. Chem., 1991, 34, 1594).Hydrolysis of carbamate 2 with hydrochloric acid providesthiophene-2-amine (Tetr. Lett, 1999, 40, 721).

Example C 2,5-dimethylthiophene available from Aldrich (Catalog #D18,364-3) Example D 1-methyl-1H-pyrrole-2,5-diamine, obtainable fromthe following synthesis strategy

Obtain 2-Chloro-1-methyl-1H-pyrrole 2 by treatment of1-methyl-1H-pyrrole 1 with thionyl chloride. Nitration of 2 with nitricacid and sulfuric acid provides compound 3. Aromatic nucleophilicsubstitution of 3 with ammonia in an autoclave affords compound 4.Catalytic hydrogenation of 4 with hydrogen in the presence of Pd/C inethanol gives 1-methyl-1H-pyrrole-2,5-diamine 5.

Example E i. 1H-pyrrol-2-amine, obtainable from the following synthesisstrategy:

Silylation of pyrrole (CAS 109-97-7) with chlorotrimethylsilane affordsN-trimethylsilylypyrrole 2 (J. Org. Chem., 1956, 21, 931). Reaction ofcompound 2 with N-chlorophthalimide 3 (may obtain by the reaction ofphthalimide (CAS 85-41-6) with tert-butyl hypochlorite accordingreference (J. Amer. Chem. Soc., 1954, 76, 3858)) gives phthalimidoderivative 4. Reduction of compound 4 with sodium borohydride givescompound 5 (Tetr. Lett., 1995, 38, 9261). Hydrolysis of compound 5 withacetic acid provides 1H-pyrrol-2-amine (Tetr. Lett., 1995, 38, 9261).

Example F 2,5-dimethylpyrrole available from Aldrich (Catalog #39,083-6)Example G Thiazol-2-amine (CAS No. 96-50-4) available from Aldrich(Catalog #123129) Example H [1,2,5]thiadiazole-3,4-diamine

Obtain 4-Amino-[1,2,5]thiadiazole-3-carboxylic acid 2 from eitherthiadiazolopyrimidinone 1 or thiadiazolopyrimidinedione 3 by hydrolysis(Advance in Heterocyclic Chemistry, Vol. 9, Academic Press, New York,1968, 107). Protection of amino group of 2 with Boc₂O and4-dimethylaminopyridine leads to compound 4. Curtius rearrangement of 4with diphenylphosphoryl azide in tert-butanol gives compound 5.Deprotection of 5 with aqueous HCl affords[1,2,5]thiadiazole-3,4-diamine6.

Example I (furan-3-yl)methanol available from Aldrich (Catalog#19,639-8) Example J 5-methylfuran-2(3H)-one available from Aldrich(Catalog #W32,930-4). Example K (furan-2-yl)methanol available fromAldrich (Furfuryl Alcohol) Example L 2-methoxyfuran available fromAldrich (Catalog #13,827-4) Example M 2-ethylpyrrole available fromAldrich (Catalog #35,771-5) Example N 2-methylpyrrole available fromLaboTest (Order No. LTBB000731) Example O 2,4-dimethylpyrrole availablefrom Aldrich (Catalog #39,083-6) Example P 3-aminothiophene availablefrom SYNCHEM OHG (Order No. ONO70) Example Q 3,4-diaminothiopheneavailable from Interbioscreen Ltd. (STOCK 45-24350) Example R5-methylthiophen-2-amine available from ChemPacific USA (Order #34086)Example S 2,5-dimethylfuran available from Aldrich (Catalog # W50,190-5)Example T 2-methylfuran available from Aldrich (Catalog # W50,290-1)

II. Keratin Dyeing Composition Components

The inventive compositions for the oxidative dyeing of keratin fiberscomprise the hair-dyeing compound described above in the hair-dyeingcompounds section and a medium suitable for dyeing. The inventivecompositions may further comprise additional components known,conventionally used, or otherwise effective for use in oxidative dyecompositions, including but limited to: developer dye compounds; couplerdye compounds; direct dyes; oxidizing agents; thickeners; chelants; pHmodifiers and buffering agents; carbonate ion sources and radicalscavenger systems; anionic, cationic, nonionic, amphoteric orzwitterionic surfactants, or mixtures thereof, anionic, cationic,nonionic, amphoteric or zwitterionic polymers, or mixtures thereof,fragrances; buffers; dispersing agents; peroxide stabilizing agents;natural ingredients, e.g. proteins and protein derivatives, and plantmaterials (e.g. aloe, chamomile and henna extracts); silicones (volatileor non-volatile, modified or non-modified), film-forming agents,ceramides, preserving agents; and opacifiers.

Some adjuvants referred to above, but not specifically described below,which are suitable are listed in the International Cosmetics IngredientDictionary and Handbook, (8^(th) ed.; The Cosmetics, Toiletry, andFragrance Association). Particularly, vol. 2, sections 3 (ChemicalClasses) and 4 (Functions) are useful in identifying specific adjuvantsto achieve a particular purpose or multipurpose.

A. Medium Suitable for Dyeing

The medium suitable for dyeing may be selected from water, or a mixtureof water and at least one organic solvent to dissolve the compounds thatwould not typically be sufficiently soluble in water. Suitable organicsolvents for use herein include, but are not limited to: C1 to C4 loweralkanols (e.g., ethanol, propanol, isopropanol), aromatic alcohols (e.g.benzyl alcohol and phenoxyethanol); polyols and polyol ethers (e.g.,carbitols, 2-butoxyethanol, propylene glycol, propylene glycolmonomethyl ether, diethylene glycol monoethyl ether, monomethyl ether,hexylene glycol, glycerol, ethoxy glycol), and propylene carbonate. Whenpresent, organic solvents are typically present in an amount rangingfrom 1% to 30%, by weight, of the composition. Preferred solvents arewater, ethanol, propanol, isopropanol, glycerol, 1,2-propylene glycol,hexylene glycol, ethoxy diglycol, and mixtures thereof. Additionalmediums suitable for dyeing may include oxidizing agents as describedbelow.

B. Auxiliary Developers

Suitable developers for use in the compositions described hereininclude, but are not limited to p-phenylenediamine derivatives, e.g.benzene-1,4-diamine (commonly known as p-phenylenediamine),2-methyl-benzene-1,4-diamine, 2-chloro-benzene-1,4-diamine,N-phenyl-benzene-1,4-diamine, N-(2-ethoxyethyl)benzene-1,4-diamine,2-[(4-amino-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol, (commonly known asN,N-bis(2-hydroxyethyl)-p-phenylenediamine)(2,5-diamino-phenyl)-methanol, 1-(2′-Hydroxyethyl)-2,5-diaminobenzene,2-(2,5-diamino-phenyl)-ethanol, N-(4-aminophenyl)benzene-1,4-diamine,2,6-dimethyl-benzene-1,4-diamine, 2-isopropyl-benzene-1,4-diamine,1-[(4-aminophenyl)amino]-propan-2-ol, 2-propyl-benzene-1,4-diamine,1,3-bis[(4-aminophenyl)(2-hydroxyethyl)amino]propan-2-ol,N⁴,N⁴,2-trimethylbenzene-1,4-diamine, 2-methoxy-benzene-1,4-diamine,1-(2,5-diaminophenyl)ethane-1,2-diol, 2,3-dimethyl-benzene-1,4-diamine,N-(4-amino-3-hydroxy-phenyl)-acetamide, 2,6-diethylbenzene-1,4-diamine,2,5-dimethylbenzene-1,4-diamine, 2-thien-2-ylbenzene-1,4-diamine,2-thien-3-ylbenzene-1,4-diamine, 2-pyridin-3-ylbenzene-1,4-diamine,1,1′-biphenyl-2,5-diamine, 2-(methoxymethyl)benzene-1,4-diamine,2-(aminomethyl)benzene-1,4-diamine, 2-(2,5-diaminophenoxy)ethanol,N-[2-(2,5-diaminophenoxy)ethyl]-acetamide,N,N-dimethylbenzene-1,4-diamine, N,N-diethylbenzene-1,4-diamine,N,N-dipropylbenzene-1,4-diamine, 2-[(4-aminophenyl)(ethyl)amino]ethanol,2-[(4-amino-3-methyl-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol,N-(2-methoxyethyl)-benzene-1,4-diamine,3-[(4-aminophenyl)amino]propan-1-ol,3-[(4-aminophenyl)-amino]propane-1,2-diol,N-{4-[(4-aminophenyl)amino]butyl}benzene-1,4-diamine, and2-[2-(2-{2-[(2,5-diaminophenyl)-oxy]ethoxy}ethoxy)ethoxy]benzene-1,4-diamine;1,3-Bis(N(2-Hydroxyethyl)-N-(4-amino-phenyl)amino)-2-propanol;2,2′-[1,2-Ethanediyl-bis-(oxy-2,1-ethanediyloxy)]-bis-benzene-1,4-diamine;N,N-Bis(2-hydroxyethyl)-p-phenylinediamine; p-aminophenol derivativessuch as: 4-amino-phenol (commonly known as p-aminophenol),4-methylamino-phenol, 4-amino-3-methyl-phenol,4-amino-2-hydroxymethyl-phenol, 4-amino-2-methyl-phenol,4-amino-1-hydroxy-2-(2′-hydroxyethylaminomethyl)benzene,4-amino-2-methoxymethyl-phenol, 5-amino-2-hydroxy-benzoic acid,1-(5-amino-2-hydroxy-phenyl)-ethane-1,2-diol,4-amino-2-(2-hydroxy-ethyl)-phenol, 4-amino-3-(hydroxymethyl)phenol,4-amino-3-fluoro-phenol, 4-amino-2-(aminomethyl)-phenol,4-amino-2-fluoro-phenol; 1-Hydroxy-2,4-diaminobenzene;1-(2′-Hydroxyethyloxy)-2,4-diaminobenzene; 2,4-Diamino-5-methylphenetol;o-phenylenediamine derivatives such as: 3,4-Diaminobenzoic acid andsalts thereof; o-aminophenol derivatives such as: 2-amino-phenol(commonly known as o-aminophenol), 2,4-diaminophenol,2-amino-5-methyl-phenol, 2-amino-6-methyl-phenol,N-(4-amino-3-hydroxy-phenyl)-acetamide, and 2-amino-4-methyl-phenol; andheterocyclic derivatives such as: pyrimidine-2,4,5,6-tetramine (commonlyknown as 2,4,5,6-tetraminopyridine), 1-methyl-1H-pyrazole-4,5-diamine,2-(4,5-diamino-1H-pyrazol-1-yl)ethanol,N²,N²-dimethyl-pyridine-2,5-diamine,2-[(3-amino-6-methoxypyridin-2-yl)amino]ethanol,6-methoxy-N²-methyl-pyridine-2,3-diamine,2,5,6-triaminopyrimidin-4(1H)-one, pyridine-2,5-diamine,1-isopropyl-1H-pyrazole-4,5-diamine,1-(4-methylbenzyl)-1H-pyrazole-4,5-diamine,1-(benzyl)-1H-pyrazole-4,5-diamine,1-(4-chlorobenzyl)-1H-pyrazole-4,5-diamine,pyrazolo[1,5-a]-pyrimidine-3,7-diamine,5,6,7-trimethylpyrazolo[1,5-a]pyrimidin-3-ylamine hydrochloride,7-methylpyrazolo[1,5-a]pyrimidin-3-ylamine hydrochloride,2,5,6,7-teramethyl-pyrazolo[1,5-a]pyrimidin-3-ylamine hydrochloride,5,7-di-tert-butylpyrazolo[1,5-a]pyrimidin-3-ylamine hydrochloride,5,7-di-trifluoromethyl-pyrazolo[1,5-a]pyrimidin-3-ylamine hydrochloride,2-methylpyrazolo[1,5-a]pyrimidin-3,7-diamine hydrochloride;4-Hydroxy-2,5,6-triaminopyrimidine;1-(2′hydroxyethyl)-amino-3,4-methylene dioxybenzene; and1-Hydroxyethyl-4,5-diaminopyrazole sulphate.

Additional developers are selected from the group consisting ofN-(3-furylmethyl)benzene-1,4-diamine;N-Thiophen-3-ylmethyl-benzene-1,4-diamine;N-(2-furylmethyl)benzene-1,4-diamine;N-Thiophen-2-ylmethyl-benzene-1,4-diamine; 4-Hydroxy-benzoic acid(2,5-diamino-benzylidene)-hydrazide;3-(2,5-Diamino-phenyl)-N-ethyl-acrylamide;2-[3-(3-Amino-phenylamino)-propenyl]-benzene-1,4-diamine;2-[3-(4-Amino-phenylamino)-propenyl]-benzene-1,4-diamine;2-(6-Methyl-pyridin-2-yl)-benzene-1,4-diamine;2-Pyridin-2-yl-benzene-1,4-diamine;2-[3-(4-Amino-phenylamino)-propenyl]-benzene-1,4-diamine;2-[3-(3-Amino-phenylamino)-propenyl]-benzene-1,4-diamine;3-(2,5-Diamino-phenyl)-N-ethyl-acrylamide;2-Thiazol-2-yl-benzene-1,4-diamine; 4-Hydroxy-benzoic acid(2,5-diamino-benzylidene)-hydrazide; 3′-Fluoro-biphenyl-2,5-diamine;2-Propenyl-benzene-1,4-diamine; 2′-Chloro-biphenyl-2,5-diamine;N-Thiophen-3-ylmethyl-benzene-1,4-diamine;N-(3-furylmethyl)benzene-1,4-diamine; 4′-Methoxy-biphenyl-2,5-diamine;N-(4-Amino-benzyl)-benzene-1,4-diamine;2-Methyl-5-[(1-H-pyrrol-2-ylmethyl)-amino]-phenol;5-[(Furan-2-ylmethyl)-amino]-2-methyl-phenol;5-Isopropylamino-2-methyl-phenol; Biphenyl-2,4,4′-triaminehydrochloride; 5-(4-Amino-phenyl)aminomethyl-benzene-1,3-diaminehydrochloride; 5-Phenylaminomethyl-benzene-1,3-diamine hydrochloride;2-[4-Amino-2-(3,5-diamino-benzylamino)-phenoxy]-ethanol hydrochloride;5-(3-Amino-phenyl)aminomethyl-benzene-1,3-diamine hydrochloride;N-(2-Amino-benzyl)-benzene-1,3-diamine hydrochloride;N-Furan-2-ylmethyl-benzene-1,3-diamine hydrochloride;2-[(3-Amino-phenylamino)-methyl]-phenol hydrochloride;4-Amino-2-propylaminomethyl-phenol; hydrochloride;N-Benzo[1,3]dioxol-5-ylmethyl-benzene-1,3-diamine hydrochloride;N-[4-Amino-2-(2-hydroxy-ethyl)-2H-pyrazol-3-yl]-3-(5-amino-2-hydroxy-phenyl)-acrylamide;hydrochloride; 4-Amino-2-(isopropylamino-methyl)-phenol; hydrochloride;4-Thiophen-3-yl-benzene-1,3-diamine; hydrochloride hydrochloride;5-Phenylaminomethyl-benzene-1,3-diamine hydrochloride;5-(3-Amino-phenyl)aminomethyl-benzene-1,3-diamine hydrochloride;4-Thiophen-3-yl-benzene-1,3-diamine; hydrochloride;2′,4′-Diamino-biphenyl-4-ol; hydrochloride;5-Cyclobutylamino-2-methyl-phenol; 5-Cyclobutylamino-2-methyl-phenol;4-Amino-2-(pyridin-3-ylaminomethyl)-phenol;5-(3-Amino-phenyl)aminomethyl-benzene-1,3-diamine hydrochloride;5-Allylaminomethyl-benzene-1,3-diamine hydrochloride;N-(4-Amino-benzyl)-benzene-1,3-diamine hydrochloride;N-Benzyl-benzene-1,3-diamine hydrochloride;3-[(3-Amino-phenylamino)-methyl]-phenol hydrochloride;N-(4-Methoxy-benzyl)-benzene-1,3-diamine hydrochloride;N-Thiophen-2-ylmethyl-benzene-1,3-diamine hydrochloride;4-Amino-2-[(2-hydroxy-5-nitro-phenylamino)-methyl]-phenol;hydrochloride; 2′,4′-Diamino-biphenyl-4-ol hydrochloride;Biphenyl-2,4,4′-triamine;5-(4-Amino-phenyl)aminomethyl-benzene-1,3-diamine hydrochloride;2-[4-Amino-2-(3,5-diamino-benzylamino)-phenoxy]-ethanol hydrochloride;5-Allylaminomethyl-benzene-1,3-diamine hydrochloride;5-(3-Amino-phenyl)aminomethyl-benzene-1,3-diamine hydrochloride;N-(4-Amino-benzyl)-benzene-1,3-diamine hydrochloride;N-Benzyl-benzene-1,3-diamine hydrochloride;3-[(3-Amino-phenylamino)-methyl]-phenol hydrochloride;N-(2-Amino-benzyl)-benzene-1,3-diamine hydrochloride;N-(4-Methoxy-benzyl)-benzene-1,3-diamine hydrochloride;N-Furan-2-ylmethyl-benzene-1,3-diamine hydrochloride;2-[(3-Amino-phenylamino)-methyl]-phenol hydrochloride;N-Thiophen-2-ylmethyl-benzene-1,3-diamine hydrochloride;N-Benzo[1,3]dioxol-5-ylmethyl-benzene-1,3-diamine hydrochloride;N-[4-Amino-2-(2-hydroxy-ethyl)-2H-pyrazol-3-yl]-3-(5-amino-2-hydroxy-phenyl)-acrylamidehydrochloride; 4-Amino-2-propylaminomethyl-phenol; hydrochloride;4-Amino-2-(isopropylamino-methyl)-phenol hydrochloride;4-Amino-2-[(2-hydroxy-5-nitro-phenylamino)-methyl]-phenol hydrochloride;2-Methyl-5-[(1-H-pyrrol-2-ylmethyl)-amino]-phenol;5-[(Furan-2-ylmethyl)-amino]-2-methyl-phenol;5-Isopropylamino-2-methyl-phenol; 5-Cyclobutylamino-2-methyl-phenol;4-Amino-2-(pyridin-3-ylaminomethyl)-phenol; and5-Cyclobutylamino-2-methyl-phenol.

Preferred developers include but are not limited to: p-phenylenediaminederivatives such as: 2-methyl-benzene-1,4-diamine; benzene-1,4-diamine;1-(2,5-diamino-phenyl)-ethanol; 2-(2,5-diamino-phenyl)-ethanol;N-(2-methoxyethyl)benzene-1,4-diamine;2-[(4-amino-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol;1-(2,5-diaminophenyl)ethane-1,2-diol;1-(2′-Hydroxyethyl)-2,5-diaminobenzene;1,3-Bis(N(2-Hydroxyethyl)-N-(4-amino-phenyl)amino)-2-propanol;2,2′-[1,2-Ethanediyl-bis-(oxy-2,1-ethanediyloxy)]-bis-benzene-1,4-diamine;N,N-Bis(2-hydroxyethyl)-p-phenylinediamine; and mixtures thereof;p-aminophenol derivatives such as: 4-amino-phenol, 4-methylamino-phenol,4-amino-3-methyl-phenol, 4-amino-2-methoxymethyl-phenol;1-(5-amino-2-hydroxy-phenyl)-ethane-1,2-diol;1-Hydroxy-2,4-diaminobenzene; 1-(2′-Hydroxyethyloxy)-2,4-diaminobenzene;4-Amino-2-aminomethylphenol; 2,4-Diamino-5-methylphenetol;4-Amino-1-hydroxy-2-(2′-hydroxyethylaminomethyl)benzene;1-methoxy-2-amino-4-(2′hydroxyethylamino)benzene; 5-aminosalicylic acidand salts thereof; and mixtures thereof; o-phenylenediamine derivativessuch as: 3,4-Diaminobenzoic acid and salts thereof; o-aminophenolderivatives such as: 2-amino-phenol, 2-amino-5-methyl-phenol,2-amino-6-methyl-phenol, N-(4-amino-3-hydroxy-phenyl)-acetamide;2-amino-4-methyl-phenol; and mixtures thereof; and heterocyclicderivatives such as: pyrimidine-2,4,5,6-tetramine;1-methyl-1H-pyrazole-4,5-diamine;2-(4,5-diamino-1H-pyrazol-1-yl)ethanol;1-(4-methylbenzyl)-1H-pyrazole-4,5-diamine;1-(benzyl)-1H-pyrazole-4,5-diamine; N²,N²-dimethyl-pyridine-2,5-diamine;4-Hydroxy-2,5,6-triaminopyrimidine;1-(2′hydroxyethyl)-amino-3,4-methylene dioxybenzene; and1-Hydroxyethyl-4,5-diaminopyrazole sulphate; and mixtures thereof.

More preferred developers include: 2-methyl-benzene-1,4-diamine;benzene-1,4-diamine; N,N-Bis(2-hydroxyethyl)-p-phenylenediamine;4-amino-phenol; 4-methylamino-phenol; 4-amino-3-methyl-phenol;1-Hydroxy-2,4-diaminobenzene; 2-amino-phenol; 2-amino-5-methyl-phenol;2-amino-6-methyl-phenol; 1-methyl-1H-pyrazole-4,5-diamine;1-Hydroxyethyl-4,5-diaminopyrazole sulphate;2-(4,5-diamino-1H-pyrazol-1-yl)ethanol; and mixtures thereof.

C. Auxiliary Couplers

Suitable couplers for use in the compositions described herein include,but are not limited to: phenols, resorcinol and naphthol derivativessuch as: naphthalene-1,7-diol, benzene-1,3-diol,4-chlorobenzene-1,3-diol, naphthalen-1-ol, 2-methyl-naphthalen-1-ol,naphthalene-1,5-diol, naphthalene-2,7-diol, benzene-1,4-diol,2-methyl-benzene-1,3-diol, 7-amino-4-hydroxy-naphthalene-2-sulfonicacid, 2-isopropyl-5-methylphenol,1,2,3,4-tetrahydro-naphthalene-1,5-diol, 2-chloro-benzene-1,3-diol,4-hydroxy-naphthalene-1-sulfonic acid, benzene-1,2,3-triol,naphthalene-2,3-diol, 5-dichloro-2-methylbenzene-1,3-diol,4,6-dichlorobenzene-1,3-diol, 2,3-dihydroxy-[1,4]naphthoquinone; and1-Acetoxy-2-methylnaphthalene; m-phenylenediamines such as:2,4-diaminophenol, benzene-1,3-diamine, 2-(2,4-diamino-phenoxy)-ethanol,2-[(3-amino-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol,2-mehyl-benzene-1,3-diamine,2-[[2-(2,4-diamino-phenoxy)-ethyl]-(2-hydroxy-ethyl)-amino]-ethanol,4-{3-[(2,4-diaminophenyl)oxy]propoxy}benzene-1,3-diamine,2-(2,4-diamino-phenyl)-ethanol,2-(3-amino-4-methoxy-phenylamino)-ethanol,4-(2-amino-ethoxy)-benzene-1,3-diamine, (2,4-diamino-phenoxy)-aceticacid, 2-[2,4-diamino-5-(2-hydroxy-ethoxy)-phenoxy]-ethanol,4-ethoxy-6-methyl-benzene-1,3-diamine,2-(2,4-diamino-5-methyl-phenoxy)-ethanol,4,6-dimethoxy-benzene-1,3-diamine,2-[3-(2-hydroxy-ethylamino)-2-methyl-phenylamino]-ethanol,3-(2,4-diamino-phenoxy)-propan-1-ol, N-[3-(dimethylamino)phenyl]urea,4-methoxy-6-methylbenzene-1,3-diamine,4-fluoro-6-methylbenzene-1,3-diamine,2-({3-[(2-hydroxyethyl)amino]-4,6-dimethoxyphenyl}-amino)ethanol,3-(2,4-diaminophenoxy)-propane-1,2-diol,2-[2-amino-4-(methylamino)-phenoxy]ethanol,2-[(5-amino-2-ethoxy-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol,2-[(3-aminophenyl)amino]ethanol,2,4-Diamino-5-(2′-hydroxyethyloxy)toluene; N,N-Dimethyl-3-ureidoaniline;N-(2-aminoethyl)benzene-1,3-diamine,4-{[(2,4-diamino-phenyl)oxy]methoxy}-benzene-1,3-diamine,1-methyl-2,6-bis(2-hydroxyethylamino)benzene; and2,4-dimethoxybenzene-1,3-diamine; m-aminophenols such as:3-amino-phenol, 2-(3-hydroxy-4-methyl-phenylamino)-acetamide,2-(3-hydroxy-phenylamino)-acetamide, 5-amino-2-methyl-phenol,5-(2-hydroxy-ethylamino)-2-methyl-phenol, 5-amino-2,4-dichloro-phenol,3-amino-2-methyl-phenol, 3-amino-2-chloro-6-methyl-phenol,5-amino-2-(2-hydroxy-ethoxy)-phenol,2-chloro-5-(2,2,2-trifluoro-ethylamino)-phenol,5-amino-4-chloro-2-methyl-phenol, 3-cyclopentylamino-phenol,5-[(2-hydroxyethyl)amino]-4-methoxy-2-methylphenol,5-amino-4-methoxy-2-methylphenol, 3-(dimethylamino)phenol,3-(diethylamino)phenol, 5-amino-4-fluoro-2-methylphenol,5-amino-4-ethoxy-2-methylphenol, 3-amino-2,4-dichloro-phenol,3-[(2-methoxyethyl)amino]phenol, 3-[(2-hydroxyethyl)amino]phenol,5-amino-2-ethyl-phenol, 5-amino-2-methoxyphenol,5-[(3-hydroxy-propyl)amino]-2-methylphenol,3-[(3-hydroxy-2-methylphenyl)-amino]propane-1,2-diol,3-[(2-hydroxyethyl)amino]-2-methylphenol;1-Methyl-2-hydroxy-4-(2′-hydroxyethyl)amino-benzene;1,3-Bis-(2,4-Diaminophenoxy)propane;1-Hydroxy-2-methyl-5-amino-6-chlorobenzene; and heterocyclic derivativessuch as: 3,4-dihydro-2H-1,4-benzoxazin-6-ol,4-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one,6-methoxyquinolin-8-amine, 4-methylpyridine-2,6-diol,2,3-dihydro-1,4-benzodioxin-5-ol, 1,3-benzodioxol-5-ol,2-(1,3-benzodioxol-5-ylamino)ethanol, 3,4-dimethylpyridine-2,6-diol,5-chloropyridine-2,3-diol, 2,6-dimethoxypyridine-3,5-diamine,1,3-benzodioxol-5-amine,2-{[3,5-diamino-6-(2-hydroxy-ethoxy)-pyridin-2-yl]oxy}-ethanol,1H-indol-4-ol, 5-amino-2,6-dimethoxypyridin-3-ol, 1H-indole-5,6-diol,1H-indol-7-ol, 1H-indol-5-ol, 1H-indol-6-ol,6-bromo-1,3-benzodioxol-5-ol, 2-aminopyridin-3-ol, pyridine-2,6-diamine,3-[(3,5-diaminopyridin-2-yl)oxy]propane-1,2-diol,5-[(3,5-diaminopyridin-2-yl)oxy]pentane-1,3-diol, 1H-indole-2,3-dione,indoline-5,6-diol, 3,5-dimethoxypyridine-2,6-diamine,6-methoxypyridine-2,3-diamine; 3,4-dihydro-2H-1,4-benzoxazin-6-amine;4-hydroxy-N-methylindole, 1H-5-methylpyrazol-5-one,1-phenyl-3-methylpyrazol-5-one,2,6-dimethylpyrazolo[1,5-b]-1,2,4-triazole,2,6-dimethyl[3,2-c]-1,2,4-triazole,6-methylpyrazolo-[1,5-a]benzimidazole, 2,6-dihydroxypyridine,2,6-dihydroxy-3,4-dimethylpyridine,5-methylpyrazolo[5,1-e]-1,2,3-triazole,5-methyl-6-chloropyrazolo[5,1-e]-1,2,3,-triazole,5-phenylpyrazolo[5,1-e]-1,2,3-triazole and its addition salts,1H-2,6-dimethylpyrazolo[1,5-b]-1,2,4-triazole tosylate,7,8-dicyano-4-methylimidazolo-[3,2-a]imidazole,2,7-dimethylpyrazolo[1,5-a]pyrimidin-5-one,2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-one, and2-methyl-5-methoxymethyl-pyrazolo[1,5-a]pyrimidin-7-one;6-Hydroxybenzomorpholine; and 3-Amino-2-methylamino-6-methoxypyridine;1-Phenyl-3-methyl-5-pyrazolone-2,4-dihydro-5,2-phenyl-3H-pyrazole-3-one.

Additional couplers are selected from the group consisting ofN-(3-furylmethyl)benzene-1,4-diamine;N-Thiophen-3-ylmethyl-benzene-1,4-diamine;N-(2-furylmethyl)benzene-1,4-diamine;N-Thiophen-2-ylmethyl-benzene-1,4-diamine; 4-Hydroxy-benzoic acid(2,5-diamino-benzylidene)-hydrazide;3-(2,5-Diamino-phenyl)-N-ethyl-acrylamide;2-[3-(3-Amino-phenylamino)-propenyl]-benzene-1,4-diamine;2-[3-(4-Amino-phenylamino)-propenyl]-benzene-1,4-diamine;2-(6-Methyl-pyridin-2-yl)-benzene-1,4-diamine;2-Pyridin-2-yl-benzene-1,4-diamine;2-[3-(4-Amino-phenylamino)-propenyl]-benzene-1,4-diamine;2-[3-(3-Amino-phenylamino)-propenyl]-benzene-1,4-diamine;3-(2,5-Diamino-phenyl)-N-ethyl-acrylamide;2-Thiazol-2-yl-benzene-1,4-diamine; 4-Hydroxy-benzoic acid(2,5-diamino-benzylidene)-hydrazide; 3′-Fluoro-biphenyl-2,5-diamine;2-Propenyl-benzene-1,4-diamine; 2′-Chloro-biphenyl-2,5-diamine;N-Thiophen-3-ylmethyl-benzene-1,4-diamine;N-(3-furylmethyl)benzene-1,4-diamine; 4′-Methoxy-biphenyl-2,5-diamine;N-(4-Amino-benzyl)-benzene-1,4-diamine;2-Methyl-5-[(1-H-pyrrol-2-ylmethyl)-amino]-phenol;5-[(Furan-2-ylmethyl)-amino]-2-methyl-phenol;5-Isopropylamino-2-methyl-phenol; Biphenyl-2,4,4′-triaminehydrochloride; 5-(4-Amino-phenyl)aminomethyl-benzene-1,3-diaminehydrochloride; 5-Phenylaminomethyl-benzene-1,3-diamine hydrochloride;2-[4-Amino-2-(3,5-diamino-benzylamino)-phenoxy]-ethanol hydrochloride;5-(3-Amino-phenyl)aminomethyl-benzene-1,3-diamine hydrochloride;N-(2-Amino-benzyl)-benzene-1,3-diamine hydrochloride;N-Furan-2-ylmethyl-benzene-1,3-diamine hydrochloride;2-[(3-Amino-phenylamino)-methyl]-phenol hydrochloride;4-Amino-2-propylaminomethyl-phenol; hydrochloride;N-Benzo[1,3]dioxol-5-ylmethyl-benzene-1,3-diamine hydrochloride;N-[4-Amino-2-(2-hydroxy-ethyl)-2H-pyrazol-3-yl]-3-(5-amino-2-hydroxy-phenyl)-acrylamide;hydrochloride; 4-Amino-2-(isopropylamino-methyl)-phenol; hydrochloride;4-Thiophen-3-yl-benzene-1,3-diamine; hydrochloride hydrochloride;5-Phenylaminomethyl-benzene-1,3-diamine hydrochloride;5-(3-Amino-phenyl)aminomethyl-benzene-1,3-diamine hydrochloride;4-Thiophen-3-yl-benzene-1,3-diamine; hydrochloride;2′,4′-Diamino-biphenyl-4-ol; hydrochloride;5-Cyclobutylamino-2-methyl-phenol; 5-Cyclobutylamino-2-methyl-phenol;4-Amino-2-(pyridin-3-ylaminomethyl)-phenol;5-(3-Amino-phenyl)aminomethyl-benzene-1,3-diamine hydrochloride;5-Allylaminomethyl-benzene-1,3-diamine hydrochloride;N-(4-Amino-benzyl)-benzene-1,3-diamine hydrochloride;N-Benzyl-benzene-1,3-diamine hydrochloride;3-[(3-Amino-phenylamino)-methyl]-phenol hydrochloride;N-(4-Methoxy-benzyl)-benzene-1,3-diamine hydrochloride;N-Thiophen-2-ylmethyl-benzene-1,3-diamine hydrochloride;4-Amino-2-[(2-hydroxy-5-nitro-phenylamino)-methyl]-phenol;hydrochloride; 2′,4′-Diamino-biphenyl-4-ol hydrochloride;Biphenyl-2,4,4′-triamine;5-(4-Amino-phenyl)aminomethyl-benzene-1,3-diamine hydrochloride;2-[4-Amino-2-(3,5-diamino-benzylamino)-phenoxy]-ethanol hydrochloride;5-Allylaminomethyl-benzene-1,3-diamine hydrochloride;5-(3-Amino-phenyl)aminomethyl-benzene-1,3-diamine hydrochloride;N-(4-Amino-benzyl)-benzene-1,3-diamine hydrochloride;N-Benzyl-benzene-1,3-diamine hydrochloride;3-[(3-Amino-phenylamino)-methyl]-phenol hydrochloride;N-(2-Amino-benzyl)-benzene-1,3-diamine hydrochloride;N-(4-Methoxy-benzyl)-benzene-1,3-diamine hydrochloride;N-Furan-2-ylmethyl-benzene-1,3-diamine hydrochloride;2-[(3-Amino-phenylamino)-methyl]-phenol hydrochloride;N-Thiophen-2-ylmethyl-benzene-1,3-diamine hydrochloride;N-Benzo[1,3]dioxol-5-ylmethyl-benzene-1,3-diamine hydrochloride;N-[4-Amino-2-(2-hydroxy-ethyl)-2H-pyrazol-3-yl]-3-(5-amino-2-hydroxy-phenyl)-acrylamidehydrochloride; 4-Amino-2-propylaminomethyl-phenol; hydrochloride;4-Amino-2-(isopropylamino-methyl)-phenol hydrochloride;4-Amino-2-[(2-hydroxy-5-nitro-phenylamino)-methyl]-phenol hydrochloride;2-Methyl-5-[(1-H-pyrrol-2-ylmethyl)-amino]-phenol;5-[(Furan-2-ylmethyl)-amino]-2-methyl-phenol;5-Isopropylamino-2-methyl-phenol; 5-Cyclobutylamino-2-methyl-phenol;4-Amino-2-(pyridin-3-ylaminomethyl)-phenol; and5-Cyclobutylamino-2-methyl-phenol.

Preferred couplers include but are not limited to: phenol, resorcinol,and naphthyl derivatives such as: naphthalene-1,7-diol,benzene-1,3-diol, 4-chlorobenzene-1,3-diol, naphthalen-1-ol,2-methyl-naphthalen-1-ol, naphthalene-1,5-diol, naphthalene-2,7-diol,benzene-1,4-diol, 2-methyl-benzene-1,3-diol, and2-isopropyl-5-methylphenol; 1,2,4-Trihydroxybenzene;1-Acetoxy-2-methylnaphthalene; and mixtures thereof; m-phenylenediaminederivatives such as: benzene-1,3-diamine,2-(2,4-diamino-phenoxy)-ethanol,4-{3-[(2,4-diaminophenyl)oxy]propoxy}benzene-1,3-diamine,2-(3-amino-4-methoxy-phenylamino)-ethanol,2-[2,4-diamino-5-(2-hydroxy-ethoxy)-phenoxy]-ethanol, and3-(2,4-diamino-phenoxy)-propan-1-ol;2,4-Diamino-5-(2′-hydroxyethyloxy)toluene; N,N-Dimethyl-3-ureidoaniline;2,4-Diamino-5-fluorotoluenesulfatehydrate;1-methyl-2,6-bis(2-hydroxyethylamino)benzene; and mixtures thereof;m-aminophenol derivatives such as: 3-amino-phenol,5-amino-2-methyl-phenol, 5-(2-hydroxy-ethylamino)-2-methyl-phenol, and3-amino-2-methyl-phenol;1-Methyl-2-hydroxy-4-(2′-hydroxyethyl)aminobenzene;1-Hydroxy-3-amino-2,4-dichlorobenzene;1,3-Bis-(2,4-Diaminophenoxy)propane;1-Hydroxy-2-methyl-5-amino-6-chlorobenzene;5-Amino-4-chloro-2-methylphenol; and mixtures thereof; and heterocyclicderivatives such as: 3,4-dihydro-2H-1,4-benzoxazin-6-ol,4-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, 1,3-benzodioxol-5-ol,1,3-benzodioxol-5-amine, 1H-indol-4-ol, 1H-indole-5,6-diol,1H-indol-7-ol, 1H-indol-5-ol, 1H-indol-6-ol, 1H-indole-2,3-dione,pyridine-2,6-diamine, 2-aminopyridin-3-ol, 4-hydroxy-N-methylindole,1H-5-methylpyrazol-5-one, 1-phenyl-3-methylpyrazol-5-one,2,6-dimethylpyrazolo[1,5-b]-1,2,4-triazole,2,6-dimethyl[3,2-c]-1,2,4-triazole,6-methylpyrazolo-[1,5-a]benzimidazole; 2,6-dihydroxypyridine;2,6-dihydroxy-3,4-dimethylpyridine; 6-Hydroxybenzomorpholine;2,6-Dihydroxy-3,4-dimethylpyridine; 3,5-Diamino-2,6-dimethoxypyridine;3-Amino-2-methylamino-6-methoxypyridine;1-Phenyl-3-methyl-5-pyrazolone-2,4-dihydro-5,2-phenyl-3H-pyrazole-3-one;and mixtures thereof.

More preferred couplers include: benzene-1,3-diol;4-chlorobenzene-1,3-diol; 2-methyl-benzene-1,3-diol;benzene-1,3-diamine; 3-amino-phenol; 5-amino-2-methyl-phenol;1-Methyl-2-hydroxy-4-(2′-hydroxyethyl)aminobenzene;4-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one; 2-aminopyridin-3-ol;1-phenyl-3-methylpyrazol-5-one;1-Phenyl-3-methyl-5-pyrazolone-2,4-dihydro-5,2-phenyl-3H-pyrazole-3-one;and mixtures thereof.

Additional preferred developers and couplers include5-methoxymethyl-2-aminophenol, 5-ethyl-2-aminophenol,5-phenyl-2-aminophenol, and 5-cyanoethyl-2-aminophenol.

Further additional preferred developers and couplers include:

-   Bicyclic fused 5-5 heteroaromatic keratin dyeing compounds with two    or three heteroatoms relating to the following compounds:

-   -   wherein Y and Z are independently selected from the group        consisting of NA¹, S and O;

-   Bicyclic 5-5 heteroaromatic compounds having a ring junction    nitrogen according to the following formulas:

-   -   wherein Y is selected from the group consisting of S and O;

-   Tricyclic 5-6-5 heteroaromatic keratin dyeing compounds having two    heteroatoms according to the following formulas:

-   -   wherein Y and Z are selected from the group consisting of NA¹,        S, and O;

-   Bicyclic 5-6 heteroaromatic keratin dyeing compounds with one ring    junction nitrogen and one or two extra heteroatoms according to the    following formulas:

-   Tricyclic fused 6-5-6 heteroaromatic keratin dyeing compounds having    one heteroatom according to the following formula:

-   -   wherein Y is independently selected from the group consisting of        NA¹, S and O;

-   5-membered aza heteroaromatic keratin dyeing compounds with an    N-hydroxy or N-amino group and derivatives thereof, according to the    following formulas:

-   -   wherein B₁, B₂, B₃, and B₄ are selected from the group        consisting of CH and N;    -   wherein the corresponding R¹, R², R³, and R⁴ is absent when B is        N;

-   Bicyclic 5-6 systems of aza heteroaromatic keratin dyeing compounds    wherein the 5-membered rings have one to three nitrogen atoms and an    N-hydroxy or N-amino group and derivatives thereof according to the    following formulas:

-   -   wherein B₁ and B₂ are independently selected from CH or N;    -   wherein the corresponding R¹ and R² is absent when B is N;

-   Bicyclic fused 5-5-membered aza heteroaromatic keratin dyeing    compounds with an N-hydroxy or N-amino group and derivatives    thereof, according to the following formulas:

-   Bicyclic fused 5-5-membered aza heteroaromatic keratin dyeing    compounds having a ring junction nitrogen and an N-hydroxy or    N-amino group and derivatives thereof, according to the following    formulas:

-   Bicyclic fused 5-5-membered aza heteroaromatic keratin dyeing    compounds having a ring junction nitrogen and an N-hydroxy or    N-amino group and derivatives thereof, according to the following    formulas:

-   wherein B₁, B₂, B₃, B₄, and B₅ are selected from the group    consisting of CH and N;-   wherein the corresponding R1, R2, R3, R4, and R5 is absent when B is    N;-   wherein all of the aforementioned R groups are the same or different    and are selected from the group consisting of:    -   (a) C-linked monovalent substituents selected from the group        consisting of:        -   (i) substituted or unsubstituted, straight or branched,            alkyl, mono- or poly-unsaturated alkyl, heteroalkyl,            aliphatic, heteroaliphatic, or heteroolefinic systems,        -   (ii) substituted or unsubstituted, mono- or poly-cyclic            aliphatic, aryl, or heterocyclic systems, and        -   (iii) substituted or unsubstituted, mono-, poly-, or            per-fluoro alkyl systems; wherein said systems of (i), (ii)            and (iii) comprise from about 1 to about 10 carbon atoms and            from about 0 to about 5 heteroatoms selected from the group            consisting of O, S, N, P, and Si;            -   wherein substituents of the substituted systems of the                C-linked monovalent substituents are selected from the                group consisting of amino, hydroxyl, alkylamino (linear,                branched, or cyclic C1-C5), dialkylamino (linear,                branched, or cyclic C1-C5), hydroxyalkylamino (linear,                branched, or cyclic C1-C5), dihydroxyalkylamino (linear,                branched, or cyclic C1-C5), arylamino or substituted                arylamino (substituents are halogen, C1-C5 alkyl, C1-C5                alkoxy, trifluoromethyl, amino, C1-C5 alkylamino),                heteroarylamino or substituted heteroarylamino                (substituents are halogen, C1-C5 alkyl, C1-C5 alkoxy,                trifluoromethyl, amino, C1-C5 alkylamino),                arylmethylamino or substituted arylmethylamino                (substituents are halogen, C1-C5 alkyl, C1-C5 alkoxy,                trifluoromethyl, amino, C1-C5 alkylamino), and                heteroarylmethylamino or substituted                heteroarylmethylamino (substituents are halogen, C1-C5                alkyl, C1-C5 alkoxy, trifluoromethyl, amino, C1-C5                alkylamino),    -   (b) S-linked monovalent substituents selected from the group        consisting of SA¹, SO₂A¹, SO₃A¹, SSA¹, SOA¹, SO₂NA¹A¹, SNA¹A²,        and SONA¹A²;    -   (c) O-linked monovalent substituents selected from the group        consisting of OA¹, and ONA¹A²;    -   (d) N-linked monovalent substituents selected from the group        consisting of NA₁A², (NA₁A²A³)⁺, NA¹OA², NA¹SA², NO₂, N═NA¹,        N═NOA¹, and NA¹CN, NA¹NA²A³;    -   (e) monovalent substituents selected from the group consisting        of COOA¹, CONA¹ ₂, CONA¹COA², C(═NA¹)NA¹A², CN, and X;    -   (f) fluoroalkyl monovalent substituents selected from the group        consisting of mono-, poly-, and per-fluoro alkyl systems        comprising from about 1 to about 12 carbon atoms and from about        0 to about 4 heteroatoms; and    -   (g) hydrogen,    -   wherein A¹, A², and A³ are monovalent and are independently        selected from the group consisting of: H; substituted or        unsubstituted, straight or branched, alkyl, mono- or        poly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic,        or heteroolefinic systems; substituted or unsubstituted, mono-        or poly-cyclic aliphatic, aryl, or heterocyclic systems; and        substituted or unsubstituted, mono-, poly-, or per-fluoro alkyl        systems, or A¹ and A² together with nitrogen atoms to which they        are bound form a ring; wherein said systems comprise from about        1 to about 10 carbon atoms and from about 0 to about 5        heteroatoms selected from the group consisting of O, S, N, P,        and Si;-   wherein X is a halogen selected from the group consisting of F, Cl,    Br, and I.

D. Direct Dyes

The inventive compositions may also comprise compatible direct dyes, inan amount sufficient to provide additional coloring, particularly withregard to intensity. Typically, such an amount will range from 0.05% to4%, by weight, of the composition. Suitable direct dyes include but arenot limited to: Acid Yellow 1, Acid Orange 3, Disperse Red 17, BasicBrown 17, Acid Black 52, Acid Black 1, Disperse Violet 4,4-Nitro-o-Phenylenediamine, 2-Nitro-p-Phenylenediamine, Picramic Acid,HC Red No. 13, 1,4-Bis-(2′-Hydroxyethyl)-amino-2-nitrobenzene, HC YellowNo. 5, HC Red No. 7, HC Blue No. 2, HC Yellow No. 4, HC Yellow No. 2, HCOrange No. 1, HC Red No. 1,2-Chloro-5-nitro-N-Hydroxyethyl-p-phenylenediamine, HC Red No.3,4-Amino-3-nitrophenol, 2-Hydroxyethylamino-5-nitroanisole,3-nitro-p-Hydroxyethylaminophenol, 2-amino-3-nitrophenol,6-nitro-o-toluidine, 3-methylamino-4-nitrophenoxyethanol,2-nitro-5-glycerymethylanaline, HC Yellow No. 11, HC Violet No. 1, HCOrange No. 2, HC Orange No. 3, HC Yellow No. 9,4-NitrophenylAminoethylurea, HC Red No. 10, HC Red No. 11, 2-Hydroxyethyl picramicacid, HC Blue No. 12, HC Yellow No. 6, Hydroxyethyl-2-nitro-p-toluidine,HC Yellow No. 12, HC Blue No. 10, HC Yellow No. 7, HC Yellow No. 10, HCBlue No. 9, N-ethyl-3-nitro PABA,4-amino-2-nitrophenyl-amine-2′-carboxylic acid,2-chloro-6-ethylamino-4-nitrophenol, 6-Nitro-2,5-pyridinediamine, HCViolet No. 2,2-amino-6-chloro-4-nitrophenol,4-hydroxypropylamino-3-nitrophenol, HC Yellow No. 13,1,2,3,4-Tetrahydro-6-nitrochinoxalin, HC Red No. 14, HC Yellow No. 15,HC Yellow No. 14, 3-Amino-6-methylamino-2-nitropyridine,2,6-diamino-3-((pyridine-3-yl)azo)pyridine, Basic Red No. 118, BasicOrange No. 69, N-(2-nitro-4-aminophenyl)-allylamine,4-[(4-Amino-3-methylphenyl)(4-Imino-3-methyl-2,5-Cyclohexadien-1-ylidene)Methyl]-2-Methyl-benzeneamine-Hydrochloride, 1H-Imidazolium,2-[[4-(dimethyl-amino)phenyl]azo]-1,3-dimethylchloride, Pyridinium,1-methyl-4-[(methylphenyl-hydrazono)methyl]-, methyl sulfate,1H-Imidazolium, 2-[(4-aminophenyl)azo]-1,3-dimethyl, chloride, Basic Red22, Basic Red 76, Basic Brown 16, Basic Yellow 57,7-(2′,4′-Dimethyl-5′-sulfophenylazo)-5-sulfo-8-hydroxynaphthalene, AcidOrange 7, Acid Red 33,1-(3′-Nitro-5′-sulfo-6′-oxophenylazo)-oxo-naphthalene chromium complex,Acid Yellow 23, Acid Blue 9, Basic Violet 14, Basic Blue 7, Basic Blue26, Sodium salt of mixture of mono- & disulfonic acids (mainly thelatter) of quinophthlanone or 2-quinolylindandione, Basic Red 2, BasicBlue 99, Disperse Red 15, Acid Violet 43, Disperse Violet 1, Acid Blue62, Pigment Blue 15, Acid Black 132, Basic Yellow 29, Disperse Black9,1-(N-Methylmorpholinium-propylamino)-4-hydroxy-anthraquinonemethylsulfate, HC Blue No. 8, HC Red No. 8, HC Green No. 1, HC Red No.9,2-Hydroxy-1,4-naphthoquinone, Acid Blue 199, Acid Blue 25, Acid Red 4,Henna Red, Indigo, Cochenille, HC Blue 14, Disperse Blue 23, DisperseBlue 3, Violet 2, Disperse Blue 377, Basic Red 51, Basic Orange 31,Basic Yellow 87, and mixtures thereof. Preferred direct dyes include butare not limited to: Disperse Black 9, HC Yellow 2, HC Yellow 4, HCYellow 15, 4-nitro-o-phenylenediamine, 2-amino-6-chloro-4-nitrophenol,HC Red 3, Disperse Violet 1, HC Blue 2, Disperse Blue 3, Disperse Blue377, Basic Red 51, Basic Orange 31, Basic Yellow 87, and mixturesthereof.

E. Oxidizing Agent

The inventive compositions may comprise an oxidizing agent, present inan amount sufficient to bleach melanin pigment in hair and/or causeformation of dye chromophores from oxidative dye precursors (includingdevelopers and/or couplers when present). Typically, such an amountranges from 1% to 20%, preferably from 3% to 15%, more preferably from6% to 12%, by weight, of the developer composition. Inorganic peroxygenmaterials capable of yielding hydrogen peroxide in an aqueous medium arepreferred, and include but are not limited to: hydrogen peroxide;inorganic alkali metal peroxides (e.g. sodium periodate and sodiumperoxide); organic peroxides (e.g. urea peroxide, melamine peroxide);inorganic perhydrate salt bleaching compounds (e.g. alkali metal saltsof perborates, percarbonates, perphosphates, persilicates, andpersulphates, preferably sodium salts thereof), which may beincorporated as monohydrates, tetrahydrates, etc.; alkali metalbromates; enzymes; and mixtures thereof. Preferred is hydrogen peroxide.

F. Thickeners

The inventive compositions may comprise a thickener in an amountsufficient to provide the composition with a viscosity so that it can bereadily applied to the hair without unduly dripping off the hair andcausing mess. Typically, such an amount will be at least 0.1%,preferably at least 0.5%, more preferably, at least 1%, by weight, ofthe composition.

Preferred for use herein are salt tolerant thickeners, including but notlimited to: xanthan, guar, hydroxypropyl guar, scleroglucan, methylcellulose, ethyl cellulose (available as AQUACOTE™), hydroxyethylcellulose (NATROSOL™), carboxymethyl cellulose, hydroxypropylmethylcellulose, microcrystalline cellulose, hydroxybutylmethyl cellulose,hydroxypropyl cellulose (available as KLUCEL™), hydroxyethyl ethylcellulose, cetyl hydroxyethyl cellulose (available as NATROSOL™) Plus330), N-vinylpyrollidone (available as POVIDONE™), Acrylates/Ceteth-20Itaconate Copolymer (available as STRUCTURE™ 3001), hydroxypropyl starchphosphate (available as STRUCTURE™ ZEA), polyethoxylated urethanes orpolycarbamyl polyglycol ester (e.g. PEG-150/Decyl/SMDI copolymer(available as ACULYN™ 44), PEG-150/Stearyl/SMDI copolymer available asACULYN™ 46), trihydroxystearin (available as THIXCIN™), acrylatescopolymer (e.g. available as ACULYN™ 33) or hydrophobically modifiedacrylate copolymers (e.g. Acrylates/Steareth-20 Methacrylate Copolymer(available as ACULYN™ 22), non-ionic amphophilic polymers comprising atleast one fatty chain and at least one hydrophilic unit selected frompolyether urethanes comprising at least one fatty chain, and blends ofCeteth-10 phosphate, Di-cetyl phosphate and Cetearyl alcohol (availableas CRODAFOS™ CES).

G. Chelants

The inventive compositions may comprise chelants in an amount sufficientto reduce the amount of metals available to interact with formulationcomponents, particularly oxidizing agents, more particularly peroxides.Typically such an amount will range from at least 0.25%, preferably atleast 0.5%, by weight, of the composition. Suitable chelants for useherein include but are not limited to: diamine-N,N′-dipolyacid,monoamine monoamide-N,N′-dipolyacid, andN,N′-bis(2-hydroxybenzyl)ethylenediamine-N,N′-diacetic acid chelants(preferably EDDS (ethylenediaminedisuccinic acid)), carboxylic acids(preferably aminocarboxylic acids), phosphonic acids (preferablyaminophosphonic acids) and polyphosphoric acids (in particular straightpolyphosphoric acids), their salts and derivatives.

H. pH Modifiers and Buffering Agents

The inventive compositions may further comprise a pH modifier and/orbuffering agent in an amount that is sufficiently effective to adjustthe pH of the composition to fall within a range from 3 to 13,preferably from 8 to 12, more preferably from 9 to 11. Suitable pHmodifiers and/or buffering agents for use herein include, but are notlimited to: ammonia, alkanolamides such as monoethanolamine,diethanolamine, triethanolamine, monopropanolamine, dipropanolamine,tripropanolamine, tripropanolamine, 2-amino-2-methyl-1-propanol, and2-amino-2-hydroxymethyl-1,3,-propandiol and guanidium salts, alkalimetal and ammonium hydroxides and carbonates, preferably sodiumhydroxide and ammonium carbonate, and acidulents such as inorganic andinorganic acids, e.g., phosphoric acid, acetic acid, ascorbic acid,citric acid or tartaric acid, hydrochloric acid, and mixtures thereof.

I. Carbonate Ion Source and Radical Scavenger System

The inventive compositions may comprise a system comprising a source ofcarbonate ions, carbamate ions and or hydrocarbonate ions, and a radicalscavenger, in a sufficient amount to reduce damage to the hair duringthe coloring process. Typically, such an amount will range from 0.1% to15%, preferably 0.1% to 10%, more preferably 1% to 7%, by weight of thecomposition, of the carbonate ion, and from 0.1% to 10%, preferably from1% to 7%, by weight of the composition, of radical scavenger.Preferably, the radical scavenger is present at an amount such that theratio of radical scavenger to carbonate ion is from 1:1 to 1:4. Theradical scavenger is preferably selected such that it is not anidentical species as the alkalizing agent.

Suitable sources for the ions include but are not limited to: sodiumcarbonate, sodium hydrogen carbonate, potassium carbonate, potassiumhydrogen carbonate, guanidine carbonate, guanidine hydrogen carbonate,lithium carbonate, calcium carbonate, magnesium carbonate, bariumcarbonate, ammonium carbonate, ammonium hydrogen carbonate and mixturesthereof. Preferred sources of carbonate ions are sodium hydrogencarbonate and potassium hydrogen carbonate. Also preferred are ammoniumcarbonate, and ammonium hydrogen carbonate.

The radical scavenger is a species that can react with a carbonateradical to convert the carbonate radical by a series of fast reactionsto a less reactive species. Preferably, when the radical scavengercomprises an N atom, it has a pKa>7 to prevent the protonation of thenitrogen. Preferred radical scavengers may be selected from the classesof alkanolamines, amino sugars, amino acids and mixtures thereof, andmay include, but are not limited to: monoethanolamine,3-amino-1-propanol, 4-amino-1-butanol,5-amino-1-pentanol,1-amino-2-propanol, 1-amino-2-butanol, 1-amino-2-pentanol,1-amino-3-pentanol, 1-amino-4-pentanol, 3-amino-2-methylpropan-1-ol,1-amino-2-methylpropan-2-ol, 3-aminopropane-1,2-diol, glucosamine,N-acetylglucosamine, glycine, arginine, lysine, proline, glutamine,histidine, serine, tryptophan and potassium, sodium and ammonium saltsof the above and mixtures thereof. Other preferred radical scavengercompounds include benzylamine, glutamic acid, imidazole,di-tert-butylhydroxytoluene, hydroquinone, catechol and mixturesthereof.

III. Methods of Manufacture

The compounds of this invention may be obtained using conventionalmethods. A general description of how to make the compounds is providedabove and specific examples are provided below. The compositions of thisinvention may also be obtained using conventional methods. The keratindyeing compositions may be formed as solutions, preferably as aqueous oraqueous-alcohol solutions. The hair dye product compositions maypreferably be formed as thick liquids, creams, gels, or emulsions whosecomposition is a mixture of the dye compound and other dye ingredientswith conventional cosmetic additive ingredients suitable for theparticular preparation.

IV. Methods of Use

The inventive keratin dyeing compositions may be used by admixing themwith a suitable oxidant, which reacts with the oxidative dye precursorsto develop the hair dye product composition. The oxidant is usuallyprovided in an aqueous composition, which normally is provided as aseparate component of the finished keratin dyeing product system andpresent in a separate container. Upon mixing the keratin dyeingcomposition, the adjuvants are provided in the hair dye composition asit is applied to the hair to achieve desired product attributes, e.g.,pH, viscosity, rheology, etc.

The keratin dyeing composition, as it is applied to the hair, can beweakly acidic, neutral or alkaline according to their composition,typically having a pH from 6 to 11, preferably from 7 to 10, morepreferably from 8 to 10. The pH of the developer composition istypically acidic, and generally the pH is from 2.5 to 6.5, preferablyfrom 3 to 5. The pH of the hair compositions may be adjusted using a pHmodifier as mentioned above.

In order to use the keratin dyeing composition, the above-describedcompositions are mixed immediately prior to use and a sufficient amountof the mixture is applied to the hair, according to the hair abundance,generally from 60 to 200 grams. Upon such preparation the hair dyecomposition is applied to the hair to be dyed and remains in contactwith the hair for an amount of time effective to dye the hair.Typically, the hair dye composition is allowed to act on the hair for 2to 60, preferably 15 to 45, more preferably, 30 minutes, at atemperature ranging from 15° to 50° C. Thereafter, the hair is rinsedwith water, to remove the hair dye composition and dried. If necessary,the hair is washed with a shampoo and rinsed, e.g., with water or aweakly acidic solution, such as a citric acid or tartaric acid solution,and dried. Optionally, a separate conditioning product may also beprovided.

Together, components of the keratin dyeing composition form a system fordyeing hair. This system may be provided as a kit comprising in a singlepackage separate containers of the keratin dyeing composition componentsor other hair treatment product, and instructions for use.

Examples

The following are non-limiting examples of the compositions of thepresent invention. The examples are given solely for the purpose ofillustration and are not to be construed as limitations of the presentinvention, as many variations thereof are possible without departingfrom the spirit and scope of the invention, which would be recognized byone of ordinary skill in the art. In the examples, all concentrationsare listed as weight percent, unless otherwise specified. As usedherein, “minors” refers to those optional components such aspreservatives, viscosity modifiers, pH modifiers, fragrances, foamboosters, and the like. As is apparent to one of ordinary skill in theart, the selection of these minors will vary depending on the physicaland chemical characteristics of the particular ingredients selected tomake the present invention as described herein.

The following compositions can be used for dyeing hair. Mix the dyeingcomposition with an equal weight of a 20-volume hydrogen peroxidesolution (6% by weight). Apply the resulting mixture to the hair andpermit it to remain in contact with the hair for 30 minutes. Shampoodyed hair and rinse with water and dry.

Examples Ingredient 1 2 3 4 5 6 7 Propylene glycol 9.5 9.5 9.5 9.5 9.59.5 9.5 Ammonium hydroxide 5 5 5 5 5 5 5 Ethoxydiglycol 4 4 4 4 4 4 4Ethanolamine 4.5 4.5 4.5 4.5 4.5 4.5 4.5 Oleic acid 1 1 1 1 1 1 1Hexylene glycol 6 6 6 6 6 6 6 Cocamidopropyl betaine 3.5 3.5 3.5 3.5 3.53.5 3.5 Oleth-10 0.3 0.3 0.3 0.3 0.3 0.3 0.3 Oleth-2 0.3 0.3 0.3 0.3 0.30.3 0.3 Dilinoleic acid 1.5 1.5 1.5 1.5 1.5 1.5 1.5 C12-C15 Pareth-3 0.50.5 0.5 0.5 0.5 0.5 0.5 Soytrimonium chloride 7 7 7 7 7 7 7 Sodiummetasilicate 0.05 0.05 0.05 0.05 0.05 0.05 0.05 Erythorbic acid 0.5 0.50.5 0.5 0.5 0.5 0.5 EDTA 0.03 0.03 0.03 0.03 0.03 0.03 0.03 Sodiumsulfite 0.3 0.3 0.3 0.3 0.3 0.3 0.3 1-Phenyl-3-methyl-5-pyrazolone 0.20.2 0.2 0.2 0.2 0.2 0.2 Thiophene-2,5-diamine 0.05 0.04 0.03 0.01 0.050.15 0.2 N,N-Bis(2-hydroxyetyl)-p- 0.1 0.02 phenylendiamine4-Aminophenol 0.2 0.02 0.3 0.2 0.4 4-Amino-2-methylphenol 0.4 0.23-Aminophenol 0.1 5-Amino-2-methylphenol 0.02 0.02 0.02 0.04 1-Naphthol0.05 Resorcinol 0.15 0.1 0.1 0.4 0.1 0.5 0.4 2-Methylresorcinol 0.41-Hydroxyethyl-4,5- 0.2 diaminopyrazole Water qs qs qs qs qs qs qsExamples Ingredient 8 9 10 11 12 13 14 Propylene glycol 9.5 9.5 9.5 9.59.5 9.5 9.5 Ammonium hydroxide 5 5 5 5 5 5 5 Ethoxydiglycol 4 4 4 4 4 44 Ethanolamine 4.5 4.5 4.5 4.5 4.5 4.5 4.5 Oleic acid 1 1 1 1 1 1 1Hexylene glycol 6 6 6 6 6 6 6 Cocamidopropyl betaine 3.5 3.5 3.5 3.5 3.53.5 3.5 Oleth-10 0.3 0.3 0.3 0.3 0.3 0.3 0.3 Oleth-2 0.3 0.3 0.3 0.3 0.30.3 0.3 Dilinoleic acid 1.5 1.5 1.5 1.5 1.5 1.5 1.5 C12-C15 Pareth-3 0.50.5 0.5 0.5 0.5 0.5 0.5 Soytrimonium chloride 7 7 7 7 7 7 7 Sodiummetasilicate 0.05 0.05 0.05 0.05 0.05 0.05 0.05 Erythorbic acid 0.5 0.50.5 0.5 0.5 0.5 0.5 EDTA 0.03 0.03 0.03 0.03 0.03 0.03 0.03 Sodiumsulfite 0.3 0.3 0.3 0.3 0.3 0.3 0.3 1-Phenyl-3-methyl-5-pyrazolone 0.20.2 0.2 0.2 0.2 0.2 0.2 N-Methyl-1H-pyrrole-2,5- 0.3 0.2 0.2 0.1 0.1 0.20.6 diamine N,N-Bis(2-hydroxyetyl)-p- 0.03 0.02 phenylendiamine4-Aminophenol 0.5 0.7 0.9 1.2 0.3 4-Amino-3-methylphenol 1 1.23-Aminophenol 0.3 5-Amino-2-methylphenol 0.4 0.4 2.5 2.5 1 0.81-Naphthol Resorcinol 0.3 0.1 0.1 0.1 0.1 0.6 0.1 2-Methylresorcinol 0.40.6 0.6 1-Hydroxyethyl-4,5- 0.2 0.2 0.4 diaminopyrazole Water qs qs qsqs qs qs qs Examples Ingredient 22 23 24 25 26 27 28 Propylene glycol9.5 9.5 9.5 9.5 9.5 9.5 9.5 Ammonium hydroxide 5 5 5 5 5 5 5Ethoxydiglycol 4 4 4 4 4 4 4 Ethanolamine 4.5 4.5 4.5 4.5 4.5 4.5 4.5Oleic acid 1 1 1 1 1 1 1 Hexylene glycol 6 6 6 6 6 6 6 Cocamidopropylbetaine 3.5 3.5 3.5 3.5 3.5 3.5 3.5 Oleth-10 0.3 0.3 0.3 0.3 0.3 0.3 0.3Oleth-2 0.3 0.3 0.3 0.3 0.3 0.3 0.3 Dilinoleic acid 1.5 1.5 1.5 1.5 1.51.5 1.5 C12-C15 Pareth-3 0.5 0.5 0.5 0.5 0.5 0.5 0.5 Soytrimoniumchloride 7 7 7 7 7 7 7 Sodium metasilicate 0.05 0.05 0.05 0.05 0.05 0.050.05 Erythorbic acid 0.5 0.5 0.5 0.5 0.5 0.5 0.5 EDTA 0.03 0.03 0.030.03 0.03 0.03 0.03 Sodium sulfite 0.3 0.3 0.3 0.3 0.3 0.3 0.31-Phenyl-3-methyl-5-pyrazolone 0.2 0.2 0.2 0.2 0.2 0.2 0.21,2,5-Thiadiazole-3,4-diamine 1 0.1 0.5 0.5 0.1 0.1 0.5N,N-Bis(2-hydroxyetyl)-p- 0.1 phenylendiamine 4-Aminophenol 0.4 0.8 0.14-Amino-2-methylphenol 0.6 0.8 3-Aminophenol 1.5 1 0.15-Amino-2-methylphenol 1.4 0.5 0.1 0.1 1-Naphthol 0.1 0.1 0.1 Resorcinol0.5 0.2 0.2 0.5 2-Methylresorcinol 0.5 0.8 0.1 1-Hydroxyethyl-4,5- 0.6 21.5 diaminopyrazole Water qs qs qs qs qs qs qs Examples Ingredient 36 3738 39 40 41 42 Propylene glycol 9.5 9.5 9.5 9.5 9.5 9.5 9.5 Ammoniumhydroxide 5 5 5 5 5 5 5 Ethoxydiglycol 4 4 4 4 4 4 4 Ethanolamine 4.54.5 4.5 4.5 4.5 4.5 4.5 Oleic acid 1 1 1 1 1 1 1 Hexylene glycol 6 6 6 66 6 6 Cocamidopropyl betaine 3.5 3.5 3.5 3.5 3.5 3.5 3.5 Oleth-10 0.30.3 0.3 0.3 0.3 0.3 0.3 Oleth-2 0.3 0.3 0.3 0.3 0.3 0.3 0.3 Dilinoleicacid 1.5 1.5 1.5 1.5 1.5 1.5 1.5 C12-C15 Pareth-3 0.5 0.5 0.5 0.5 0.50.5 0.5 Soytrimonium chloride 7 7 7 7 7 7 7 Sodium metasilicate 0.050.05 0.05 0.05 0.05 0.05 0.05 Erythorbic acid 0.5 0.5 0.5 0.5 0.5 0.50.5 EDTA 0.03 0.03 0.03 0.03 0.03 0.03 0.03 Sodium sulfite 0.3 0.3 0.30.3 0.3 0.3 0.3 1-Phenyl-3-methyl-5-pyrazolone 0.2 0.2 0.2 0.2 0.2 0.20.2 Thiophen-2-amine 0.3 0.5 0.4 0.3 2,5-dimethylfuran 0.5 0.4 0.3N,N-Bis(2-hydroxyetyl)-p- 0.1 0.1 0.3 0.1 0.3 phenylendiaminep-Phenylenediamine 0.4 0.4 4-Aminophenol 0.5 0.1 0.2 0.1 0.24-Amino-3-methylphenol 1 1 3-Aminophenol 0.3 0.2 0.25-Amino-2-methylphenol 0.4 0.2 0.5 0.4 0.2 0.5 1-Naphthol 0.1 0.1Resorcinol 0.3 0.2 0.4 0.3 0.2 0.4 0.3 2-Methylresorcinol 0.4 0.2 0.21-Hydroxyethyl-4,5- 0.5 0.1 0.3 0.5 0.1 0.3 diaminopyrazole Water qs qsqs qs qs qs qs Examples Ingredient 43 44 45 46 47 48 49 Propylene glycol9.5 9.5 9.5 9.5 9.5 9.5 9.5 Ammonium hydroxide 5 5 5 5 5 5 5Ethoxydiglycol 4 4 4 4 4 4 4 Ethanolamine 4.5 4.5 4.5 4.5 4.5 4.5 4.5Oleic acid 1 1 1 1 1 1 1 Hexylene glycol 6 6 6 6 6 6 6 Cocamidopropylbetaine 3.5 3.5 3.5 3.5 3.5 3.5 3.5 Oleth-10 0.3 0.3 0.3 0.3 0.3 0.3 0.3Oleth-2 0.3 0.3 0.3 0.3 0.3 0.3 0.3 Dilinoleic acid 1.5 1.5 1.5 1.5 1.51.5 1.5 C12-C15 Pareth-3 0.5 0.5 0.5 0.5 0.5 0.5 0.5 Soytrimoniumchloride 7 7 7 7 7 7 7 Sodium metasilicate 0.05 0.05 0.05 0.05 0.05 0.050.05 Erythorbic acid 0.5 0.5 0.5 0.5 0.5 0.5 0.5 EDTA 0.03 0.03 0.030.03 0.03 0.03 0.03 Sodium sulfite 0.3 0.3 0.3 0.3 0.3 0.3 0.31-Phenyl-3-methyl-5-pyrazolone 0.2 0.2 0.2 0.2 0.2 0.2 0.21H-pyrrol-2-amine 0.3 0.5 0.4 0.3 2,5-dimethylpyrrole 0.5 0.4 0.3N,N-Bis(2-hydroxyetyl)-p- 0.1 0.1 0.3 0.1 0.3 phenylendiaminep-Phenylenediamine 0.4 0.4 4-Aminophenol 0.5 0.1 0.2 0.1 0.24-Amino-3-methylphenol 1 1 3-Aminophenol 0.3 0.2 0.25-Amino-2-methylphenol 0.4 0.2 0.5 0.4 0.2 0.5 1-Naphthol 0.1 0.1Resorcinol 0.3 0.2 0.4 0.3 0.2 0.4 0.3 2-Methylresorcinol 0.4 0.2 0.21-Hydroxyethyl-4,5- 0.5 0.1 0.3 0.5 0.1 0.3 diaminopyrazole Water qs qsqs qs qs qs qs

While particular embodiments of the present invention have beenillustrated and described, it would be obvious to those skilled in theart that various other changes and modifications can be made withoutdeparting from the spirit and scope of the invention. It is thereforeintended to cover in the appended claims all such changes andmodifications that are within the scope of this invention.

All documents cited in the Background, Summary of the Invention, andDetailed Description of the Invention are, in relevant part,incorporated herein by reference; the citation of any document is not tobe construed as an admission that it is prior art with respect to thepresent invention.

1. A keratin dyeing composition comprising: (A) a medium suitable fordyeing; and (B) one or more five-membered heteroaromatic keratin dyeingcompounds with one heteroatom relating to the following compound:

wherein R¹, R², R³, and R⁴ are the same or different and are selectedfrom the group consisting of: (a) C-linked monovalent substituentsselected from the group consisting of: (i) substituted or unsubstituted,straight or branched, alkyl, mono- or poly-unsaturated alkyl,heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems, (ii)substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, orheterocyclic systems, and (iii) substituted or unsubstituted, mono-,poly-, or per-fluoro alkyl systems; wherein said systems of (i), (ii)and (iii) comprise from about 1 to about 10 carbon atoms and from about0 to about 5 heteroatoms selected from the group consisting of O, S, N,P, and Si; (b) S-linked monovalent substituents selected from the groupconsisting of SA¹, SO₂A¹, SO₃A¹, SSA¹, SOA¹, SO₂NA¹A², SNA¹A², andSONA¹A²; (c) O-linked monovalent substituents selected from the groupconsisting of OA¹, and ONA¹A²; (d) N-linked monovalent substituentsselected from the group consisting of NA¹A², (NA¹A²A³)⁺, NA¹OA², NA¹SA²,NO₂, N═NA¹, N═NOA¹, NA¹CN, NA¹NA²A³; (e) monovalent substituentsselected from the group consisting of COOA¹, CONA¹ ₂, CONA¹COA²,C(═NA¹)NA¹A², CN, and X; (f) fluoroalkyl monovalent substituentsselected from the group consisting of mono-, poly-, and per-fluoro alkylsystems comprising from about 1 to about 12 carbon atoms and from about0 to about 4 heteroatoms; and (g) hydrogen wherein A¹, A², and A³ aremonovalent and are independently selected from the group consisting of:H; substituted or unsubstituted, straight or branched, alkyl, mono- orpoly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, orheteroolefinic systems; substituted or unsubstituted, mono- orpoly-cyclic aliphatic, aryl, or heterocyclic systems; and substituted orunsubstituted, mono-, poly-, or per-fluoro alkyl systems; wherein saidsystems comprise from about 1 to about 10 carbon atoms and from about 0to about 5 heteroatoms selected from the group consisting of O, S, N, P,and Si; wherein X is a halogen selected from the group consisting of F,Cl, Br, and I.
 2. The composition of claim 1 wherein said five-memberedheteroaromatic keratin dyeing compounds are selected from the groupconsisting of Thiophene-2,5-diamine; N-Methyl-thiophene-2,5-diamine;N-Ethyl-thiophene-2,5-diamine; N-Propyl-thiophene-2,5-diamine;2-(5-Amino-thiophen-2-ylamino)-ethanol;3-(5-Amino-thiophen-2-ylamino)-propan-1-ol;3-(5-Amino-thiophen-2-ylamino)-propane-1,2-diol;N-Phenyl-thiophene-2,5-diamine; N-Benzyl-thiophene-2,5-diamine;N-Thiophen-2-ylmethyl-thiophene-2,5-diamine;N-Furan-2-ylmethyl-thiophene-2,5-diamine;3-Methyl-thiophene-2,5-diamine; 3,N′5′-Dimethyl-thiophene-2,5-diamine;N′5′-Ethyl-3-methyl-thiophene-2,5-diamine;3-Methyl-N′5′-propyl-thiophene-2,5-diamine;2-(5-Amino-4-methyl-thiophen-2-ylamino)-ethanol;3-(5-Amino-4-methyl-thiophen-2-ylamino)-propan-1-ol;3-(5-Amino-4-methyl-thiophen-2-ylamino)-propane-1,2-diol;3,4-Dimethyl-thiophene-2,5-diamine;3,4,N-Trimethyl-thiophene-2,5-diamine;N-Ethyl-3,4-dimethyl-thiophene-2,5-diamine;3,4-Dimethyl-N-propyl-thiophene-2,5-diamine;2-(5-Amino-3,4-dimethyl-thiophen-2-ylamino)-ethanol;3-(5-Amino-3,4-dimethyl-thiophen-2-ylamino)-propan-1-ol;3-(5-Amino-3,4-dimethyl-thiophen-2-ylamino)-propane-1,2-diol;N,N-Dimethyl-thiophene-2,5-diamine; N,N-Diethyl-thiophene-2,5-diamine;N-Ethyl-N-methyl-thiophene-2,5-diamine;5-Pyrrolidin-1-yl-thiophen-2-ylamine;2-[(5-Amino-thiophen-2-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(5-Amino-thiophen-2-yl)-methyl-amino]-ethanol;2-[(5-Amino-thiophen-2-yl)-ethyl-amino]-ethanol;3-Methoxy-thiophene-2,5-diamine; 3-Ethoxy-thiophene-2,5-diamine;3-Phenoxy-thiophene-2,5-diamine; 3-Benzyloxy-thiophene-2,5-diamine;3-Fluoro-thiophene-2,5-diamine; 3-Chloro-thiophene-2,5-diamine;2,5-Diamino-thiophene-3-carbonitrile; 3-Phenyl-thiophene-2,5-diamine;[2,3′]Bithiophenyl-2′,5′-diamine; 3-Furan-2-yl-thiophene-2,5-diamine;Thiophene-2,3-diamine; 4-Methyl-thiophene-2,3-diamine;4,5-Dimethyl-thiophene-2,3-diamine;4-Methoxy-5-methyl-thiophene-2,3-diamine;4-Chloro-thiophene-2,3-diamine; 5-Phenyl-thiophene-2,3-diamine;4-Phenyl-thiophene-2,3-diamine; 4-Thiazol-2-yl-thiophene-2,3-diamine;5-Furan-2-yl-thiophene-2,3-diamine; 5-(pyrrolidin-1-yl)thiophen-2-amine;5-Furan-2-yl-thiophene-2,3-diamine; 5-amino-thiophen-2-ol;Thiophen-2-amine, 5-methylthiophene-2-amine, 4-methylthiophen-2-amine,4-Methoxy-thiophen-2-amine, Thiophene-3,4-diamine,4-Amino-thiophen-3-ol, thiophene-2,4-diamine, 3-methoxythiophene,2-methoxythiophene, 2-aminothiophene-3-carboxylic acid,2,3-dihydrothieno[3,4-b][1,4]dioxine, thiophen-2-ol, thiophen-3-ol,thiophen-2,3-diol, thiophen-2,4-diol, thiophen-2,5-diol,thiophen-3,4-diol, 2-aminothiophen-3-ol, 2-aminothiophen-4-ol,2-aminothiophen-5-ol, 3-aminothiophen-2-ol, 3-aminothiophen-4-ol,3-aminothiophen-5-ol, 4-aminothiophen-2-ol, 4-aminothiophen-5-ol,5-aminothiophen-4-ol, 2-methoxythiophen-3-amine,2-methoxythiophen-4-amine, 2-methoxythiophen-5-amine,3-methoxythiophen-2-amine, 3-methoxythiophen-4-amine,3-methoxythiophen-5-amine, 4-methoxythiophen-2-amine,2-methoxythiophen-3-ol, 2-methoxythiophen-4-ol, 2-methoxythiophen-5-ol,3-methoxythiophen-2-ol, 3-methoxythiophen-4-ol, 3-methoxythiophen-5-ol,4-methoxythiophen-2-ol, 2,5-dimethoxythiophene, 2,3-dimethoxythiophene,2,4-dimethoxythiophene, 3-methylthiophen-2-amine,2-methylthiophen-3-amine, 4-methylthiophen-3-amine,5-methylthiophen-3-amine, 2-cyanothiophen-3,4-diamine,2-cyanothiophen-3,5-diamine, 3-cyanothiophen-2-amine,3-cyanothiophen-5-amine, 3-cyanothiophen-2,4-diamine,3-cyanothiophen-2,5-diol, 2-cyanothiophen-3,4-diol,2-cyanothiophen-3,5-diol, 3-cyanothiophen-2-ol, 3-cyanothiophen-4-ol,3-cyanothiophen-5-ol, 3-cyanothiophen-2,4-diol,3-chlorothiophen-2,5-diamine, 3,4-chlorothiophen-2,5-diamine,2-chlorothiophen-3-amine, 2-chlorothiophen-4-amine,2-chlorothiophen-5-amine, 2-chlorothiophen-3,4-diamine,2-chlorothiophen-3,5-diamine, 3-chlorothiophen-2-amine,3-chlorothiophen-4-amine, 3-chlorothiophen-5-amine,3-chlorothiophen-2,4-diamine, 3-chlorothiophen-2,5-diol,2-chlorothiophen-3-ol, 2-chlorothiophen-4-ol, 2-chlorothiophen-5-ol,2-chlorothiophen-3,4-diol, 2-chlorothiophen-3,5-diol,3-chlorothiophen-2-ol, 3-chlorothiophen-4-ol, 3-chlorothiophen-5-ol,3-chlorothiophen-2,4-diol, 5-aminothiophen-2-carboxylic acid,3-aminothiophen-2-carboxylic acid, 4-aminothiophen-2-carboxylic acid,3,4-diaminothiophen-2-carboxylic acid, 3,5-diaminothiophen-2-carboxylicacid, 4,5-diaminothiophen-2-carboxylic acid,2-aminothiophen-3-carboxylic acid, 4-aminothiophen-3-carboxylic acid,5-aminothiophen-3-carboxylic acid, 2,4-diaminothiophen-3-carboxylicacid, 2,5-diaminothiophen-3-carboxylic acid,4,5-diaminothiophen-3-carboxylic acid, 5-hydroxythiophen-2-carboxylicacid, 3-hydroxythiophen-2-carboxylic acid,4-hydroxythiophen-2-carboxylic acid, 3,4-dihydroxythiophen-2-carboxylicacid, 3,5-dihydroxythiophen-2-carboxylic acid,4,5-dihydroxythiophen-2-carboxylic acid, 2-hydroxythiophen-3-carboxylicacid, 4-hydroxythiophen-3-carboxylic acid,5-hydroxythiophen-3-carboxylic acid, 2,4-dihydroxythiophen-3-carboxylicacid, 2,5-dihydroxythiophen-3-carboxylic acid,4,5-dihydroxythiophen-3-carboxylic acid, 5-methoxythiophen-2-carboxylicacid, 3-methoxythiophen-2-carboxylic acid,4-methoxythiophen-2-carboxylic acid, 3,4-dimethoxythiophen-2-carboxylicacid, 3,5-dimethoxythiophen-2-carboxylic acid,4,5-dimethoxythiophen-2-carboxylic acid, 2-methoxythiophen-3-carboxylicacid, 4-methoxythiophen-3-carboxylic acid,5-methoxythiophen-3-carboxylic acid, 2,4-dimethoxythiophen-3-carboxylicacid, 2,5-dimethoxythiophen-3-carboxylic acid,4,5-dimethoxythiophen-3-carboxylic acid; 2,5-dimethylthiophene,2-methylthiophene, 2,3-dimethylthiophene, 3,4-dimethylthiophene,2,4-dimethylthiophene, thiophene-3-amine, and 5-methyl-thiophen-2-amine.3. The composition of claim 1 wherein said five-membered heteroaromatickeratin dyeing compounds are selected from the group consisting ofthiophene-2,5-diamine; 5-(pyrrolidin-1-yl)thiophen-2-amine;2,5-diamino-thiophene-3-carbonitrile; thiophene-2,3-diamine;4-methylthiophene-2,3-diamine; N-Methyl-thiophene-2,5-diamine;3-Methyl-thiophene-2,5-diamine; thiophene-2-amine;5-methylthiophene-2-amine; 4-methylthiophen-2-amine;thiophene-3,4-diamine; 4-aminothiophen-3-ol; thiophene-2,4-diamine;3-methoxythiophene; 2-methoxythiophene; 2-aminothiophene-3-carboxylicacid; 2,3-dihydrothieno[3,4-b][1,4]dioxine; 2,5-dimethylthiophene;2-methylthiophene; 3,4-dimethylthiophene; 2,4-dimethylthiophene;thiophen-2-ol; thiophen-2,4-diol; thiophen-2,5-diol;5-methyl-thiophen-2-amine; and thiophene-3-amine.
 4. A keratin dyeingcomposition comprising: (A) a medium suitable for dyeing; and (B) one ormore five-membered heteroaromatic keratin dyeing compounds with one,heteroatom relating to the following compound:

wherein R¹, R², R³, and R⁴ are the same or different and are selectedfrom the group consisting of: (a) C-linked monovalent substituentsselected from the group consisting of: (i) substituted or unsubstituted,straight or branched, alkyl, mono- or poly-unsaturated alkyl,heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinic systems, (ii)substituted or unsubstituted, mono- or poly-cyclic aliphatic, aryl, orheterocyclic systems, and (iii) substituted or unsubstituted, mono-,poly-, or per-fluoro alkyl systems; wherein said systems of (i), (ii)and (iii) comprise from about 1 to about 10 carbon atoms and from about0 to about 5 heteroatoms selected from the group consisting of O, S, N,P, and Si; (b) S-linked monovalent substituents selected from the groupconsisting of SA¹, SO₂A¹, SO₃A¹, SSA¹, SOA¹, SO₂NA¹A², SNA¹A², andSONA¹A²; (c) O-linked monovalent substituents selected from the groupconsisting of OA¹, and ONA¹A²; (d) N-linked monovalent substituentsselected from the group consisting of NA¹A², (NA¹A²A³)⁺, NA¹OA², NA¹SA²,NO₂, N═NA¹, N═NOA¹, NA¹CN, NA¹NA²A³; (e) monovalent substituentsselected from the group consisting of COOA¹, CONA¹ ₂, CONA¹COA²,C(═NA¹)NA¹A², CN, and X; (f) fluoroalkyl monovalent substituentsselected from the group consisting of mono-, poly-, and per-fluoro alkylsystems comprising from about 1 to about 12 carbon atoms and from about0 to about 4 heteroatoms; and (g) hydrogen wherein A¹, A², and A³ aremonovalent and are independently selected from the group consisting of:H; substituted or unsubstituted, straight or branched, alkyl, mono- orpoly-unsaturated alkyl, heteroalkyl, aliphatic, heteroaliphatic, orheteroolefinic systems; substituted or unsubstituted, mono- orpoly-cyclic aliphatic, aryl, or heterocyclic systems; and substituted orunsubstituted, mono-, poly-, or per-fluoro alkyl systems; wherein saidsystems comprise from about 1 to about 10 carbon atoms and from about 0to about 5 heteroatoms selected from the group consisting of O, S, N, P,and Si; wherein X is a halogen selected from the group consisting of F,Cl, Br, and I.
 5. The composition of claim 4 wherein said five-memberedheteroaromatic keratin dyeing compounds are selected from the groupconsisting of Furan-2,5-diamine; N-Methyl-furan-2,5-diamine;N-Ethyl-furan-2,5-diamine; N-Propyl-furan-2,5-diamine;2-(5-Amino-furan-2-ylamino)-ethanol;3-(5-Amino-furan-2-ylamino)-propan-1-ol;3-(5-Amino-furan-2-ylamino)-propane-1,2-diol;N,N-Dimethyl-furan-2,5-diamine; N,N-Diethyl-furan-2,5-diamine;N-Ethyl-N-methyl-furan-2,5-diamine; 5-Pyrrolidin-1-yl-furan-2-ylamine;2-[(5-Amino-furan-2-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(5-Amino-furan-2-yl)-methyl-amino]-ethanol;2-[(5-Amino-furan-2-yl)-ethyl-amino]-ethanol;3-Fluoro-furan-2,5-diamine; 3-Chloro-furan-2,5-diamine;3-Trifluoromethyl-furan-2,5-diamine;5-Amino-2-methylamino-furan-3-carbonitrile;2,5-Diamino-furan-3-carbonitrile;5-Amino-2-ethylamino-furan-3-carbonitrile;5-Amino-2-propylamino-furan-3-carbonitrile;5-Amino-2-(2-hydroxy-ethylamino)-furan-3-carbonitrile;5-Amino-2-(3-hydroxy-propylamino)-furan-3-carbonitrile;5-Amino-2-(2,3-dihydroxy-propylamino)-furan-3-carbonitrile;5-Amino-2-dimethylamino-furan-3-carbonitrile;5-Amino-2-diethylamino-furan-3-carbonitrile;5-Amino-2-(ethyl-methyl-amino)-furan-3-carbonitrile;5-Amino-2-pyrrolidin-1-yl-furan-3-carbonitrile;5-Amino-2-[bis-(2-hydroxy-ethyl)-amino]-furan-3-carbonitrile;5-Amino-2-[(2-hydroxy-ethyl)-methyl-amino]-furan-3-carbonitrile;5-Amino-2-[ethyl-(2-hydroxy-ethyl)-amino]-furan-3-carbonitrile;5-amino-furan-2-ol; furan-3,4-diamine, 4-amino-furan-3-ol,4-aminofuran-3-carboxylic acid, furan-2-amine, 5-methylfuran-2-amine,4-methylfuran-2-amine, 4-methoxyfuran-2-amine, furan-2,4-diamine,3-methoxyfuran, 2-methoxyfuran, 2-aminofuran-3-carboxylic acid,furan-2-ol, furan-3-ol, furan-2,3-diol, furan-2,4-diol, furan-2,5-diol,furan-3,4-diol, 2-aminofuran-3-ol, 2-aminofuran-4-ol, 2-aminofuran-5-ol,3-aminofuran-2-ol, 3-aminofuran-4-ol, 4-aminofuran-2-ol,4-aminofuran-5-ol, 5-aminofuran-4-ol, 2-methoxyfuran-3-amine,2-methoxyfuran-4-amine, 2-methoxyfuran-5-amine, 3-methoxyfuran-2-amine,3-methoxyfuran-4-amine, 3-methoxyfuran-5-amine, 4-methoxyfuran-2-amine,2-methoxyfuran-3-ol, 2-methoxyfuran-4-ol, 2-methoxyfuran-5-ol,3-methoxyfuran-2-ol, 3-methoxyfuran-4-ol, 3-methoxyfuran-5-ol,4-methoxyfuran-2-ol, 2,5-dimethoxyfuran, 2,3-dimethoxyfuran,2,4-dimethoxyfuran, 3-methylfuran-2-amine, 2-methylfuran-3-amine,4-methylfuran-3-amine, 5-methylfuran-3-amine, 3-cyanofuran-2,5-diamine,2-cyanofuran-3-amine, 2-cyanofuran-4-amine, 2-cyanofuran-5-amine,2-cyanofuran-3,4-diamine, 2-cyanofuran-3,5-diamine,3-cyanofuran-2-amine, 3-cyanofuran-4-amine, 3-cyanofuran-5-amine,3-cyanofuran-2,4-diamine, 3-cyanofuran-2,5-diol, 2-cyanofuran-3-ol,2-cyanofuran-4-ol, 2-cyanofuran-5-ol, 2-cyanofuran-3,4-diol,2-cyanofuran-3,5-diol, 3-cyanofuran-2-ol, 3-cyanofuran-4-ol,3-cyanofuran-5-ol, 3-cyanofuran-2,4-diol, 3-chlorofuran-2,5-diamine,2-chlorofuran-3-amine, 2-chlorofuran-4-amine, 2-chlorofuran-5-amine,2-chlorofuran-3,4-diamine, 2-chlorofuran-3,5-diamine,3-chlorofuran-2-amine, 3-chlorofuran-4-amine, 3-chlorofuran-5-amine,3-chlorofuran-2,4-diamine, 3-chlorofuran-2,5-diol, 2-chlorofuran-3-ol,2-chlorofuran-4-ol, 2-chlorofuran-5-ol, 2-chlorofuran-3,4-diol,2-chlorofuran-3,5-diol, 3-chlorofuran-2-ol, 3-chlorofuran-4-ol,3-chlorofuran-5-ol, 3-chlorofuran-2,4-diol, 5-aminofuran-2-carboxylicacid, 3-aminofuran-2-carboxylic acid, 4-aminofuran-2-carboxylic acid,3,4-diaminofuran-2-carboxylic acid, 3,5-diaminofuran-2-carboxylic acid,4,5-diaminofuran-2-carboxylic acid, 2-aminofuran-3-carboxylic acid,4-aminofuran-3-carboxylic acid, 5-aminofuran-3-carboxylic acid,2,4-diaminofuran-3-carboxylic acid, 2,5-diaminofuran-3-carboxylic acid,4,5-diaminofuran-3-carboxylic acid, 5-hydroxyfuran-2-carboxylic acid,3-hydroxyfuran-2-carboxylic acid, 4-hydroxyfuran-2-carboxylic acid,3,4-dihydroxyfuran-2-carboxylic acid, 3,5-dihydroxyfuran-2-carboxylicacid, 4,5-dihydroxyfuran-2-carboxylic acid, 2-hydroxyfuran-3-carboxylicacid, 4-hydroxyfuran-3-carboxylic acid, 5-hydroxyfuran-3-carboxylicacid, 2,4-dihydroxyfuran-3-carboxylic acid,2,5-dihydroxyfuran-3-carboxylic acid, 4,5-dihydroxyfuran-3-carboxylicacid, 5-methoxyfuran-2-carboxylic acid, 3-methoxyfuran-2-carboxylicacid, 4-methoxyfuran-2-carboxylic acid, 3,4-dimethoxyfuran-2-carboxylicacid, 3,5-dimethoxyfuran-2-carboxylic acid,4,5-dimethoxyfuran-2-carboxylic acid, 2-methoxyfuran-3-carboxylic acid,4-methoxyfuran-3-carboxylic acid, 5-methoxyfuran-3-carboxylic acid,2,4-dimethoxyfuran-3-carboxylic acid, 2,5-dimethoxyfuran-3-carboxylicacid, 4,5-dimethoxyfuran-3-carboxylic acid, 2,5-dimethylfuran,2-methylfuran, 2,3-dimethylfuran, 3,4-dimethylfuran, 2,4-dimethylfuran,furan-3-methanol, 5-methyl-furan-2-ol, and (furan-2-yl)methanol.
 6. Thecomposition of claim 4 wherein said five-membered heteroaromatic keratindyeing compounds are selected from the group consisting offuran-2,5-diamine; 2-(5-Amino-1H-furan-2-ylamino)-ethanol;2,5-diamino-furan-3-carbonitrile; furan-2,3-diamine;4-methylfuran-2,3-diamine; 3-Methyl-furan-2,5-diamine; furan-2-amine;furan-3,4-diamine; 4-amino-furan-3-ol; 4-amino-furan-3-carboxylic acid;2,5-dimethylfuran; 2-methylfuran; 3,4-dimethylfuran; 2,4-dimethylfuran;2-methoxyfuran; furan-3-methanol; 5-methyl-furan-2-ol; and(furan-2-yl)methanol.
 7. A keratin dyeing composition comprising: (A) amedium suitable for dyeing; and (B) one or more thiazole compoundsselected from the group consisting of thiazole-2,5-diamine;N′2′-Methyl-thiazole-2,5-diamine; N′2′-Ethyl-thiazole-2,5-diamine;N′2′-Propyl-thiazole-2,5-diamine; 2-(5-Amino-thiazol-2-ylamino)-ethanol;3-(5-Amino-thiazol-2-ylamino)-propan-1-ol;3-(5-Amino-thiazol-2-ylamino)-propane-1,2-diol;N′2′,N′2′-Dimethyl-thiazole-2,5-diamine;N′2′,N′2′-Diethyl-thiazole-2,5-diamine;N′2′-Ethyl-N′-2′-methyl-thiazole-2,5-diamine;N′2′-Ethyl-N′2′-propyl-thiazole-2,5-diamine;2-[(5-Amino-thiazol-2-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(5-Amino-thiazol-2-yl)-methyl-amino]-ethanol;2-[(5-Amino-thiazol-2-yl)-ethyl-amino]-ethanol;N′5′-Methyl-thiazole-2,5-diamine; N′5′-Ethyl-thiazole-2,5-diamine;N′5′-Propyl-thiazole-2,5-diamine; 2-(2-Amino-thiazol-5-ylamino)-ethanol;3-(2-Amino-thiazol-5-ylamino)-propan-1-ol;3-(2-Amino-thiazol-5-ylamino)-propane-1,2-diol;N′5′,N′5′-Dimethyl-thiazole-2,5-diamine;N′5′,N′5′-Diethyl-thiazole-2,5-diamine;N′5′-Ethyl-N′5′-methyl-thiazole-2,5,-diamine;5-Pyrrolidin-1-yl-thiazol-2-ylamine;2-[(2-Amino-thiazol-5-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(2-Amino-thiazol-5-yl)-methyl-amino]-ethanol;2-[(2-Amino-thiazol-5-yl)-ethyl-amino]-ethanol;4-Methyl-thiazole-2,5-diamine; 4-Ethyl-thiazole-2,5-diamine;2-(2,5-Diamino-thiazol-4-yl)-ethanol; 4-Phenyl-thiazole-2,5-diamine;4-Thiophen-2-yl-thiazole-2,5-diamine; 4-Furan-2-yl-thiazole-2,5-diamine;[2,4′]Bithiazolyl-2′,5′-diamine; 4-Methoxy-thiazole-2,5-diamine;4-Ethoxy-thiazole-2,5-diamine; 4-Phenoxy-thiazole-2,5-diamine;4-Fluoro-thiazole-2,5-diamine; 4-Chloro-thiazole-2,5-diamine;4-Trifluoromethyl-thiazole-2,5-diamine; and2,5-Diamino-thiazole-4-carbonitrile; thiazole-4,5-diamine;5-aminothiazol-4-ol; 5-amino-furan-2-ol; 2-amino-thiazol-5-ol;thiazol-5-amine, 2-methylthiazol-5-amine, 2-phenylthiazol-5-amine,thiazol-2-amine, 5-methylthiazol-2-amine, thiazol-5-ol,2-methylthiazol-5-ol, 2-phenylthiazol-5-ol, thiazol-2-ol,5-methylthiazol-2-ol, 5-phenylthiazol-2-ol, 2-aminothiazol-5-ol,2-amino-4-methylthiazol-5-ol, 2-amino-4-phenylthiazol-5-ol,2-amino-4-ethylthiazol-5-ol, 5-aminothiazol-2-ol,5-amino-4-methylthiazol-2-ol, 5-amino-4-phenylthiazol-2-ol,5-amino-4-ethylthiazol-2-ol, thiazol-2,5-diol, 4-methylthiazol-2,5-diol,4-phenylthiazol-2,5-diol, thiazol-2,5-diol, 4-methylthiazol-2,5-diol,4-phenylthiazol-2,5-diol, thiazol-2,5-diamine,4-methylthiazol-2,5-diamine, 4-phenylthiazol-2,5-diamine,5-methoxythiazole, 5-methoxy-2-methylthiazole,5-methoxy-2-phenylthiazole, 2-methoxythiazole,2-methoxy-5-methylthiazole, 2-methoxy-5-phenylthiazole,2,5-dimethoxythiazole, 2,5-dimethoxy-4-methylthiazole,2,5-dimethoxy-4-phenylthiazole, 5-aminothiazol-4-carbonitrile,5-amino-2-methylthiazol-4-carbonitrile,5-amino-2-phenylthiazol-4-carbonitrile, 5-hydroxythiazol-4-carbonitrile,5-hydroxy-2-methylthiazol-4-carbonitrile,5-hydroxy-2-phenylthiazol-4-carbonitrile,2,5-dihydroxythiazol-4-carbonitrile,2,5-dimethoxythiazol-4-carbonitrile, 4-chlorothiazol-5-ol,4-chloro-2-methylthiazol-5-ol, 4-chloro-2-phenylthiazol-5-ol,4-chlorothiazol-2,5-diol, 4-chlorothiazol-5-amine,4-chloro-2-methylthiazol-5-amine, 4-chloro-2-phenylthiazol-5-amine,4-chlorothiazol-2,5-diamine, 4-fluorothiazol-2,5-diamine,4-trifluoromethylthiazol-2,5-diamine, 2-methylthiazol-5-amine,2-methylthiazol-5-ol, thiazol-2,4-diol, 2-methylthiazol-5-amine,2-ethylthiazol-5-amine, 2-(thiazol-5-ylamino)ethanol, and3-(thiazol-5-ylamino)propane-1,2-diol.
 8. The composition of claim 7wherein said thiazole is selected from the group consisting ofthiazole-2,5-diamine; 5-Pyrrolidin-1-yl-thiazol-2-ylamine;2-(5-Amino-thiazol-2-ylamino)-ethanol; thiazole-4,5-diamine;thiazol-2,4,5-triamine; 4-aminothiazol-5-ol; thiazol-5-amine;2-methyl-thiazol-5-ylamine; thiazol-2-amine; 4-methylthiazol-2-amine;thiazol-2,4-diamine; thiazol-5-ol; thiazol-2,5-diol; andthiazol-2,4-diol.
 9. A keratin dyeing composition comprising: (A) amedium suitable for dyeing; and (B) one or more five-memberedheteroaromatic keratin dyeing compounds with two heteroatoms relating tothe following compound:

wherein R¹, R², and R⁴ are the same or different and are selected fromthe group consisting of: (a) C-linked monovalent substituents selectedfrom the group consisting of: (i) substituted or unsubstituted, straightor branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl,aliphatic, heteroaliphatic, or heteroolefinic systems, (ii) substitutedor unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclicsystems, and (iii) substituted or unsubstituted, mono-, poly-, orper-fluoro alkyl systems; wherein said systems of (i), (ii) and (iii)comprise from about 1 to about 10 carbon atoms and from about 0 to about5 heteroatoms selected from the group consisting of O, S, N, P, and Si;(b) S-linked monovalent substituents selected from the group consistingof SA¹, SO₂A¹, SO₃A¹, SSA¹, SOA¹, SO₂NA¹A², SNA¹A², and SONA¹A²; (c)O-linked monovalent substituents selected from the group consisting ofOA¹, and ONA¹A²; (d) N-linked monovalent substituents selected from thegroup consisting of NA¹A², (NA¹A²A³)⁺, NA¹OA², NA¹SA², NO₂, N═NA¹,N═NOA¹, NA¹CN, NA¹NA²A³; (e) monovalent substituents selected from thegroup consisting of COOA¹, CONA¹ ₂, CONA¹COA², C(═NA¹)NA¹A², CN, and X;(f) fluoroalkyl monovalent substituents selected from the groupconsisting of mono-, poly-, and per-fluoro alkyl systems comprising fromabout 1 to about 12 carbon atoms and from about 0 to about 4heteroatoms; and (g) hydrogen wherein A¹, A², and A³ are monovalent andare independently selected from the group consisting of: H; substitutedor unsubstituted, straight or branched, alkyl, mono- or poly-unsaturatedalkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinicsystems; substituted or unsubstituted, mono- or poly-cyclic aliphatic,aryl, or heterocyclic systems; and substituted or unsubstituted, mono-,poly-, or per-fluoro alkyl systems; wherein said systems comprise fromabout 1 to about 10 carbon atoms and from about 0 to about 5 heteroatomsselected from the group consisting of O, S, N, P, and Si; wherein X is ahalogen selected from the group consisting of F, Cl, Br, and I.
 10. Thecomposition of claim 9 wherein said five-membered heteroaromatic keratindyeing compounds are selected from the group consisting ofoxazole-2,5-diamine; N′2′-Methyl-oxazole-2,5-diamine;N′2′-Ethyl-oxazole-2,5-diamine; N′2′-Propyl-oxazole-2,5-diamine;2-(5-Amino-oxazol-2-ylamino)-ethanol;3-(5-Amino-oxazol-2-ylamino)-propan-1-ol;3-(5-Amino-oxazol-2-ylamino)-propane-1,2-diol;N′2′-Phenyl-oxazole-2,5-diamine; N′2′-Thiophen-2-yl-oxazole-2,5-diamine;N′2′-Furan-2-yl-oxazole-2,5-diamine;N′2′-Thiazol-2-yl-oxazole-2,5-diamine; N′5′-Methyl-oxazole-2,5-diamine;N′5′-Ethyl-oxazole-2,5-diamine; N′5′-Propyl-oxazole-2,5-diamine;2-(2-Amino-oxazol-5-ylamino)-ethanol;3-(2-Amino-oxazol-5-ylamino)-propan-1-ol;3-(2-Amino-oxazol-5-ylamino)-propane-1,2-diol;N′5′-Phenyl-oxazole-2,5-diamine; N′5′-Thiophen-2-yl-oxazole-2,5-diamine;N′5′-Furan-2-yl-oxazole-2,5-diamine;N′5′-Thiazol-2-yl-oxazole-2,5-diamine; 4-Methyl-oxazole-2,5-diamine;4,N′2′-Dimethyl-oxazole-2,5-diamine;N′2′-Ethyl-4-methyl-oxazole-2,5-diamine;4-Methyl-N′2′-propyl-oxazole-2,5-diamine;2-(5-Amino-4-methyl-oxazol-2-ylamino)-ethanol;3-(5-Amino-4-methyl-oxazol-2-ylamino)-propan-1-ol;3-(5-Amino-4-methyl-oxazol-2-ylamino)-propane-1,2-diol;4-Methyl-N′2′-phenyl-oxazole-2,5-diamine;4-Methyl-N′2′-thiophen-2-yl-oxazole-2,5-diamine;N′2′-Furan-2-yl-4-methyl-oxazole-2,5-diamine;4-Methyl-N′2′-thiazol-2-yl-oxazole-2,5-diamine;4-Methyl-N′5′-thiazol-2-yl-oxazole-2,5-diamine;4-Methyl-N′5′-thiazol-2-yl-oxazole-2,5-diamine;4,N′5′-Dimethyl-oxazole-2,5-diamine;N′5′-Ethyl-4-methyl-oxazole-2,5-diamine;4-Methyl-N′5′-propyl-oxazole-2,5-diamine;2-(2-Amino-4-methyl-oxazol-5-ylamino)-ethanol;3-(2-Amino-4-methyl-oxazol-5-ylamino)-propan-1-ol;3-(2-Amino-4-methyl-oxazol-5-ylamino)-propane-1,2-diol;4-Methyl-N′5′-phenyl-oxazole-2,5-diamine;4-Methyl-N′5′-thiophen-2-yl-oxazole-2,5-diamine;N′5′-Furan-2-yl-4-methyl-oxazole-2,5-diamine;4-Phenyl-oxazole-2,5-diamine; 4-Thiophen-2-yl-oxazole-2,5-diamine;4-Furan-2-yl-oxazole-2,5-diamine; 4-Thiazol-2-yl-oxazole-2,5-diamine;4-Fluoro-oxazole-2,5-diamine; 4-Chloro-oxazole-2,5-diamine;4-Trifluoromethyl-oxazole-2,5-diamine;2,5-Diamino-oxazole-4-carbonitrile; 4-Methoxy-oxazole-2,5-diamine;4-Ethoxy-oxazole-2,5-diamine; 2-amino-thiazol-5-ol; 2-amino-oxazol-5-ol;oxazol-5-amine, 2-methyloxazol-5-amine, 2-phenyloxazol-5-amine,oxazol-2-amine, 5-methyl-oxazol-2-amine, oxazol-5-ol,2-methyloxazol-5-ol, 2-phenyloxazol-5-ol, oxazol-2-ol,5-methyl-oxazol-2-ol, 5-phenyloxazol-2-ol, 2-aminooxazol-5-ol,2-amino-4-methyloxazol-5-ol, 2-amino-4-phenyloxazol-5-ol,2-amino-4-ethyloxazol-5-ol, 5-aminooxazol-2-ol,5-amino-4-methyloxazol-2-ol, 5-amino-4-phenyloxazol-2-ol,5-amino-4-ethyloxazol-2-ol, oxazol-2,5-diol, 4-methyloxazol-2,5-diol,4-phenyloxazol-2,5-diol, oxazol-2,5-diol, 4-methyloxazol-2,5-diol,4-phenyloxazol-2,5-diol, oxazol-2,5-diamine, 4-methyloxazol-2,5-diamine,4-phenyloxazol-2,5-diamine, 5-methoxyoxazole, 5-methoxy-2-methyl-oxazol,5-methoxy-2-phenyl-oxazol, 2-methoxyoxazole, 2-methoxy-5-methyloxazole,2-methoxy-5-phenyloxazole, 2,5-dimethoxyoxazole,2,5-dimethoxy-4-methyloxazole, 2,5-dimethoxy-4-phenyloxazole,5-aminooxazol-4-carbonitrile, 5-amino-2-methyloxazol-4-carbonitrile,5-amino-2-phenyloxazol-4-carbonitrile, 5-hydroxyoxazol-4-carbonitrile,5-hydroxy-2-methyloxazol-4-carbonitrile,5-hydroxy-2-phenyloxazol-4-carbonitrile,2,5-dihydroxyoxazol-4-carbonitrile, 2,5-dimethoxyoxazol-4-carbonitrile,4-chlorooxazol-5-ol, 4-chloro-2-methyloxazol-5-ol,4-chloro-2-phenyloxazol-5-ol, 4-chlorooxazol-2,5-diol,4-chlorooxazol-5-amine, 4-chloro-2-methyloxazol-5-amine,4-chloro-2-phenyloxazol-5-amine, 4-chlorooxazol-2,5-diamine,4-fluorooxazol-2,5-diamine, 4-trifluoromethyloxazol-2,5-diamine,2-methyloxazol-5-amine, 2-methyloxazol-5-ol, oxazol-2,4-diol,2-methyloxazol-5-amine, 2-ethyloxazol-5-amine,2-(oxazol-5-ylamino)ethanol, and 3-(oxazol-5-ylamino)propane-1,2-diol.11. The composition of claim 9 wherein said five-membered heteroaromatickeratin dyeing compounds are selected from the group consisting ofoxazol-2,5-diamine; 5-Pyrrolidin-1-yl-oxazol-2-ylamine;2-(5-Amino-oxazol-2-ylamino)-ethanol; oxazol-4,5-diamine;oxazol-2,4,5-triamine; 4-aminooxazol-5-ol; oxazol-5-amine;2-methyl-oxazol-5-amine; oxazol-2-amine; 4-methyloxazol-2-amine;oxazol-2,4-diamine; oxazol-5-ol; oxazol-2,5-diol; and oxazol-2,4-diol.12. A keratin dyeing composition comprising: (A) a medium suitable fordyeing; and (B) one or more five-membered heteroaromatic keratin dyeingcompounds with two heteroatoms relating to the following compound:

wherein R¹, R², and R³ are the same or different and are selected fromthe group consisting of: (a) C-linked monovalent substituents selectedfrom the group consisting of: (i) substituted or unsubstituted, straightor branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl,aliphatic, heteroaliphatic, or heteroolefinic systems, (ii) substitutedor unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclicsystems, and (iii) substituted or unsubstituted, mono-, poly-, orper-fluoro alkyl systems; wherein said systems of (i), (ii) and (iii)comprise from about 1 to about 10 carbon atoms and from about 0 to about5 heteroatoms selected from the group consisting of O, S, N, P, and Si;(b) S-linked monovalent substituents selected from the group consistingof SA¹, SO₂A¹, SO₃A¹, SSA¹, SOA¹, SO₂NA¹A², SNA¹A², and SONA¹A²; (c)O-linked monovalent substituents selected from the group consisting ofOA¹, and ONA¹A²; (d) N-linked monovalent substituents selected from thegroup consisting of NA¹A², (NA¹A²A³)⁺, NA¹OA², NA¹SA², NO₂, N═NA¹,N═NOA¹, NA¹CN, NA¹NA²A³; (e) monovalent substituents selected from thegroup consisting of COOA¹, CONA¹ ₂, CONA¹COA², C(═NA¹)NA¹A², CN, and X;(f) fluoroalkyl monovalent substituents selected from the groupconsisting of mono-, poly-, and per-fluoro alkyl systems comprising fromabout 1 to about 12 carbon atoms and from about 0 to about 4heteroatoms; and (g) hydrogen wherein A¹, A², and A³ are monovalent andare independently selected from the group consisting of: H; substitutedor unsubstituted, straight or branched, alkyl, mono- or poly-unsaturatedalkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinicsystems; substituted or unsubstituted, mono- or poly-cyclic aliphatic,aryl, or heterocyclic systems; and substituted or unsubstituted, mono-,poly-, or per-fluoro alkyl systems; wherein said systems comprise fromabout 1 to about 10 carbon atoms and from about 0 to about 5 heteroatomsselected from the group consisting of O, S, N, P, and Si; wherein X is ahalogen selected from the group consisting of F, Cl, Br, and I.
 13. Thecomposition of claim 12 wherein said five-membered heteroaromatickeratin dyeing compounds are selected from the group consisting ofisothiazole-4,5-diamine, 3-Methyl-isothiazole-4,5-diamine,3-Ethyl-isothiazole-4,5-diamine, 3-Propyl-isothiazole-4,5-diamine,2-(4,5-Diamino-isothiazol-3-yl)-ethanol,3-(4,5-Diamino-isothiazol-3-yl)-propan-1-ol,3-(4,5-Diamino-isothiazol-3-yl)-propane-1,2-diol,3-Furan-2-yl-isothiazole-4,5-diamine,3-Thiophen-2-yl-isothiazole-4,5-diamine,3-Phenyl-isothiazole-4,5-diamine,3-Furan-2-ylmethyl-isothiazole-4,5-diamine,3-Thiophen-2-ylmethyl-isothiazole-4,5-diamine,3-Methoxy-isothiazole-4,5-diamine, 3-Ethoxy-isothiazole-4,5-diamine,3-Phenoxy-isothiazole-4,5-diamine, 3-Benzyloxy-isothiazole-4,5-diamine,3-Fluoro-isothiazole-4,5-diamine, 3-Chloro-isothiazole-4,5-diamine,isothiazole-3,4-diamine, 4-aminoisothiazol-5-ol,5-Methyl-isothiazole-3,4-diamine, 5-amino-isothiazol-4-ol,4-amino-isothiazol-5-ol, isothiazol-5-amine, 3-methylisothiazol-5-amine,3-phenylisothiazol-5-amine, isothiazol-4-amine,3-methylisothiazol-5-amine, isothiazol-5-ol, 3-methylisothiazol-5-ol,3-phenylisothiazol-5-ol, isothiazol-4-ol, 5-methylisothiazol-3-ol,5-phenylisothiazol-3-ol, 3-aminoisothiazol-5-ol, 5-aminoisothiazol-3-ol,5-amino-4-chloroisothiazol-2-ol, 5-amino-4-cyanoisothiazol-2-ol,isothiazol-3,5-diol, 4-chloroisothiazol-3,5-diol,4-cyanoisothiazol-3,5-diol, 4-methoxyisothiazol-3,5-diol,4-fluoroisothiazol-3,5-diol, 4-bromoisothiazol-3,5-diol,4-ethoxyisothiazol-3,5-diol, isothiazol-3,5-diamine,4-chloroisothiazol-3,5-diamine, 4-methoxyisothiazol-3,5-diamine,4-fluoroisothiazol-3,5-diamine, 4-cyanoisothiazol-3,5-diamine,5-methoxyisothiazole, 5-methoxy-3-methylisothiazol,5-methoxy-3-phenylisothiazole, 4-methoxyisothiazole,4-methoxy-3-methylisothiazole, 4-methoxy-3-phenylisothiazole,3,5-dimethoxyisothiazole, 3,5-dimethoxy-4-chloroisothiazole,3,5-dimethoxy-4-methoxyisothiazole, 3,5-dimethoxy-4-fluoroisothiazole,3,5-dimethoxy-4-ethoxyisothiazole, 5-aminoisothiazol-4-carbonitrile,5-amino-3-methylisothiazol-4-carbonitrile,5-amino-3-phenylisothiazol-4-carbonitrile,5-hydroxyisothiazol-4-carbonitrile,5-hydroxy-3-methylisothiazol-4-carbonitrile,5-hydroxy-3-phenylisothiazol-4-carbonitrile,3,5-dihydroxyisothiazol-4-carbonitrile,3,5-dimethoxyisothiazol-4-carbonitrile, 4-chloroisothiazol-5-ol,4-chloro-3-methylisothiazol-5-ol, 4-chloro-3-phenylisothiazol-5-ol,4-chloroisothiazol-3,5-diol, 4-chloroisothiazol-5-amine,4-chloro-3-methylisothiazol-5-amine,4-chloro-3-phenylisothiazol-5-amine, 4-chloroisothiazol-3,5-diamine,4-fluoroisothiazol-3,5-diamine, 4-trifluoromethylisothiazol-3,5-diamine,3-methylisothiazol-5-amine, isothiazol-3,4-diol, isothiazol-3,4-diamine,3-methylisothiazol-5-amine, 3-ethylisothiazol-5-amine,2-(isothiazol-5-ylamino)ethanol, and3-(isothiazol-5-ylamino)propane-1,2-diol.
 14. The composition of claim12 wherein said five-membered heteroaromatic keratin dyeing compoundsare selected from the group consisting of Isothiazole-4,5-diamine;3-methyl-isothiazole-4,5-diamine; 4-aminoisothiazol-5-ol;3-Methoxy-isothiazole-4,5-diamine; isothiazol-5-amine;3-methylisothiazol-5-amine; 3-methylisothiazol-5-amine; isothiazol-5-ol;3-methylisothiazol-5-ol; 3-aminoisothiazol-5-ol; 5-aminoisothiazol-3-ol;and isothiazol-3,5-diol.
 15. A keratin dyeing composition comprising:(A) a medium suitable for dyeing; and (B) one or more five-memberedheteroaromatic keratin dyeing compounds with two heteroatoms relating tothe following compound:

wherein R¹, R², and R³ are the same or different and are selected fromthe group consisting of: (a) C-linked monovalent substituents selectedfrom the group consisting of: (i) substituted or unsubstituted, straightor branched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl,aliphatic, heteroaliphatic, or heteroolefinic systems, (ii) substitutedor unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclicsystems, and (iii) substituted or unsubstituted, mono-, poly-, orper-fluoro alkyl systems; wherein said systems of (i), (ii) and (iii)comprise from about 1 to about 10 carbon atoms and from about 0 to about5 heteroatoms selected from the group consisting of O, S, N, P, and Si;(b) S-linked monovalent substituents selected from the group consistingof SA¹, SO₂A¹, SO₃A¹, SSA¹, SOA¹, SO₂NA¹A², SNA¹A², and SONA¹A²; (c)O-linked monovalent substituents selected from the group consisting ofOA¹, and ONA¹A²; (d) N-linked monovalent substituents selected from thegroup consisting of NA¹A², (NA¹A²A³)⁺, NA¹OA², NA¹SA², NO₂, N═NA¹,N═NOA¹, NA¹CN, NA¹NA²A³; (e) monovalent substituents selected from thegroup consisting of COOA¹, CONA¹ ₂, CONA¹COA², C(═NA¹)NA¹A², CN, and X;(f) fluoroalkyl monovalent substituents selected from the groupconsisting of mono-, poly-, and per-fluoro alkyl systems comprising fromabout 1 to about 12 carbon atoms and from about 0 to about 4heteroatoms; and (g) hydrogen wherein A¹, A², and A³ are monovalent andare independently selected from the group consisting of: H; substitutedor unsubstituted, straight or branched, alkyl, mono- or poly-unsaturatedalkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinicsystems; substituted or unsubstituted, mono- or poly-cyclic aliphatic,aryl, or heterocyclic systems; and substituted or unsubstituted, mono-,poly-, or per-fluoro alkyl systems; wherein said systems comprise fromabout 1 to about 10 carbon atoms and from about 0 to about 5 heteroatomsselected from the group consisting of O, S, N, P, and Si; wherein X is ahalogen selected from the group consisting of F, Cl, Br, and I.
 16. Thecomposition of claim 15 wherein said five-membered heteroaromatickeratin dyeing compounds are selected from the group consisting ofIsoxazole-4,5-diamine, 3-Methyl-isoxazole-4,5-diamine,3-Ethyl-isoxazole-4,5-diamine, 3-Propyl-isoxazole-4,5-diamine,2-(4,5-Diamino-isoxazol-3-yl)-ethanol,3-(4,5-Diamino-isoxazol-3-yl)-propan-1-ol,3-(4,5-Diamino-isoxazol-3-yl)-propane-1,2-diol,3-Furan-2-yl-isoxazole-4,5-diamine,3-Thiophen-2-yl-isoxazole-4,5-diamine, 3-Phenyl-isoxazole-4,5-diamine,3-Furan-2-ylmethyl-isoxazole-4,5-diamine,3-Thiophen-2-ylmethyl-isoxazole-4,5-diamine,3-Methoxy-isoxazole-4,5-diamine, 3-Ethoxy-isoxazole-4,5-diamine,3-Phenoxy-isoxazole-4,5-diamine, 3-Benzyloxy-isoxazole-4,5-diamine,3-Fluoro-isoxazole-4,5-diamine, 3-Chloro-isoxazole-4,5-diamine,Isoxazole-3,4-diamine, 5-Methyl-isoxazole-3,4-diamine,5-amino-isoxazol-4-ol, 4-amino-isoxazol-5-ol, isoxazol-5-amine,3-methylisoxazol-5-amine, 3-phenylisoxazol-5-amine, isoxazol-4-amine,3-methylisoxazol-5-amine, isoxazol-5-ol, 3-methylisoxazol-5-ol,3-phenylisoxazol-5-ol, isoxazol-4-ol, 5-methylisoxazol-3-ol,5-phenylisoxazol-3-ol, 3-aminoisoxazol-5-ol, 5-aminoisoxazol-3-ol,5-amino-4-chloroisoxazol-2-ol, 5-amino-4-cyanoisoxazol-2-ol,isoxazol-3,5-diol, 4-chloroisoxazol-3,5-diol, 4-cyanoisoxazol-3,5-diol,4-methoxyisoxazol-3,5-diol, 4-fluoroisoxazol-3,5-diol,4-bromoisoxazol-3,5-diol, 4-ethoxyisoxazol-3,5-diol,isoxazol-3,5-diamine, 4-chloroisoxazol-3,5-diamine,4-methoxyisoxazol-3,5-diamine, 4-fluoroisoxazol-3,5-diamine,4-cyanoisoxazol-3,5-diamine, 5-methoxyisoxazole,5-methoxy-3-methylisoxazol, 5-methoxy-3-phenylisoxazole,4-methoxyisoxazole, 4-methoxy-3-methylisoxazole,4-methoxy-3-phenylisoxazole, 3,5-dimethoxyisoxazole,3,5-dimethoxy-4-chloroisoxazole, 3,5-dimethoxy-4-methoxyisoxazole,3,5-dimethoxy-4-fluoroisoxazole, 3,5-dimethoxy-4-ethoxyisoxazole,5-aminoisoxazol-4-carbonitrile, 5-amino-3-methylisoxazol-4-carbonitrile,5-amino-3-phenylisoxazol-4-carbonitrile,5-hydroxyisoxazol-4-carbonitrile,5-hydroxy-3-methylisoxazol-4-carbonitrile,5-hydroxy-3-phenylisoxazol-4-carbonitrile,3,5-dihydroxyisoxazol-4-carbonitrile,3,5-dimethoxyisoxazol-4-carbonitrile, 4-chloroisoxazol-5-ol,4-chloro-3-methylisoxazol-5-ol, 4-chloro-3-phenylisoxazol-5-ol,4-chloroisoxazol-3,5-diol, 4-chloroisoxazol-5-amine,4-chloro-3-methylisoxazol-5-amine, 4-chloro-3-phenylisoxazol-5-amine,4-chloroisoxazol-3,5-diamine, 4-fluoroisoxazol-3,5-diamine,4-trifluoromethylisoxazol-3,5-diamine, 3-methylisoxazol-5-amine,3-methylisoxazol-5-ol, isoxazol-3,4-diol, isoxazol-3,4-diamine,3-methylisoxazol-5-amine, 3-ethylisoxazol-5-amine,2-(isoxazol-5-ylamino)ethanol, and3-(isoxazol-5-ylamino)propane-1,2-diol.
 17. The composition of claim 15wherein said five-membered heteroaromatic keratin dyeing compounds areselected from the group consisting of Isoxazole-4,5-diamine;3-methyl-isoxazole-4,5-diamine; 4-aminoisoxazol-5-ol;3-Methoxy-isoxazole-4,5-diamine; isoxazol-5-amine;3-methylisoxazol-5-amine; 3-methylisoxazol-5-amine; isoxazol-5-ol;3-methylisoxazol-5-ol; 3-aminoisoxazol-5-ol; 5-aminoisoxazol-3-ol; andisoxazol-3,5-diol.
 18. A keratin dyeing composition comprising: (A) amedium suitable for dyeing; and (B) one or more imidazole compoundsselected from the group consisting of 3H-imidazole-2,4-diamine;N′2′-Methyl-3H-imidazole-2,4-diamine;N′2′-Ethyl-3H-imidazole-2,4-diamine;N′2′-Propyl-3H-imidazole-2,4-diamine;2-(5-Amino-1H-imidazol-2-ylamino)-ethanol;3-(5-Amino-1H-imidazol-2-ylamino)-propan-1-ol;3-(5-Amino-1H-imidazol-2-ylamino)-propane-1,2-diol;N′2′-Phenyl-3H-imidazole-2,4-diamine;N′2′-Thiophen-2-yl-3H-imidazole-2,4-diamine;N′2′-Furan-2-yl-3H-imidazole-2,4-diamine;N′2′-Thiazol-2-yl-3H-imidazole-2,4-diamine;N′4′-Methyl-3H-imidazole-2,4-diamine;N′4′-Ethyl-3H-imidazole-2,4-diamine;N′4′-Propyl-3H-imidazole-2,4-diamine;2-(2-Amino-3H-imidazol-4-ylamino)-ethanol;3-(2-Amino-3H-imidazol-4-ylamino)-propan-1-ol;3-(2-Amino-3H-imidazol-4-ylamino)-propane-1,2-diol;N′4′-Phenyl-3H-imidazole-2,4-diamine;N′4′-Thiophen-2-yl-3H-imidazole-2,4-diamine;N′4′-Furan-2-yl-3H-imidazole-2,4-diamine;N′4′-Thiazol-2-yl-3H-imidazole-2,4-diamine;5-Methyl-3H-imidazole-2,4-diamine;5,N′2′-Dimethyl-3H-imidazole-2,4-diamine;N′2′-Ethyl-5-methyl-3H-imidazole-2,4-diamine;5-Methyl-N′2′-propyl-3H-imidazole-2,4-diamine;2-(5-Amino-4-methyl-1H-imidazol-2-ylamino)-ethanol;3-(5-Amino-4-methyl-1H-imidazol-2-ylamino)-propan-1-ol;3-(5-Amino-4-methyl-1H-imidazol-2-ylamino)-propane-1,2-diol;5-Methyl-N′2′-phenyl-3H-imidazole-2,4-diamine;5-Methyl-N′2′-thiophen-2-yl-3H-imidazole-2,4-diamine;N′2′-Furan-2-yl-5-methyl-3H-imidazole-2,4-diamine;5-Methyl-N′2′-thiazol-2-yl-3H-imidazole-2,4-diamine;5-Methyl-N′4′-thiazol-2-yl-3H-imidazole-2,4-diamine;5,N′4′-Dimethyl-3H-imidazole-2,4-diamine;N′4′-Ethyl-5-methyl-3H-imidazole-2,4-diamine;5-Methyl-N′4′-propyl-3H-imidazole-2,4-diamine;2-(2-Amino-5-methyl-3H-imidazol-4-ylamino)-ethanol;3-(2-Amino-5-methyl-3H-imidazol-4-ylamino)-propan-1-ol;3-(2-Amino-5-methyl-3H-imidazol-4-ylamino)-propane-1,2-diol;5-Methyl-N′4′-phenyl-3H-imidazole-2,4-diamine;5-Methyl-N′4′-thiophen-2-yl-3H-imidazole-2,4-diamine;N′4′-Furan-2-yl-5-methyl-3H-imidazole-2,4-diamine;5-Phenyl-3H-imidazole-2,4-diamine;5-Thiophen-2-yl-3H-imidazole-2,4-diamine;5-Furan-2-yl-3H-imidazole-2,4-diamine;5-Thiazol-2-yl-3H-imidazole-2,4-diamine;5-Fluoro-3H-imidazole-2,4-diamine; 5-Chloro-3H-imidazole-2,4-diamine;5-Trifluoromethyl-3H-imidazole-2,4-diamine;2,5-Diamino-1H-imidazole-4-carbonitrile;5-Methoxy-3H-imidazole-2,4-diamine; 5-Ethoxy-3H-imidazole-2,4-diamine;1H-imidazol-2,4,5-triamine; 1-methyl-1H-imidazol-2,4,5-triamine;1-phenyl-1H-imidazol-2,4,5-triamine; 4,5-diamino-1H-imidazol-2-ol;4,5-diamino-1-methyl-1H-imidazol-2-ol;4,5-diamino-1-phenyl-1H-imidazol-2-ol; 2-methyl-1H-imidazol-4,5-diamine;1,2-dimethyl-1H-imidazol-4,5-diamine;2-methyl-1-phenyl-1H-imidazol-4,5-diamine;2-methyl-4-amino-1H-imidazol-4-ol;1,2-dimethyl-4-amino-1H-imidazol-4-ol;2-methyl-4-amino-1-phenyl-1H-imidazol-4-ol;4-amino-1-methyl-1H-imidazol-2,5-diol;4-amino-1-phenyl-1H-imidazol-2,5-diol; 4-amino-1H-imidazol-2,5-diol;1H-imidazol-4,5-diamine; 1-methyl-1H-imidazol-4,5-diamine;1-phenyl-1H-imidazol-4,5-diamine; 4-amino-isoxazol-5-ol;1H-imidazol-5-amine, 1-methyl-1H-imidazol-5-amine,1-phenyl-1H-imidazol-5-amine, 1H-imidazol-2-amine,1-methyl-1H-imidazol-2-amine, 1H-imidazol-5-ol,1-methyl-1H-imidazol-5-ol, 1-phenyl-1H-imidazol-5-ol, 1H-imidazol-2-ol,1-methyl-1H-imidazol-2-ol, 1-phenyl-1H-imidazol-2-ol,2-amino-1H-imidazol-5-ol, 2-amino-1-methyl-1H-imidazol-5-ol,2-amino-1-phenyl-1H-imidazol-5-ol, 2-amino-1-ethyl-1H-imidazol-5-ol,5-amino-1H-imidazol-2-ol, 5-amino-1-methyl-1H-imidazol-2-ol,5-amino-1-phenyl-1H-imidazol-2-ol, 5-amino-1-ethyl-1H-imidazol-2-ol,1H-imidazol-2,5-diol, 1-methyl-1H-imidazol-2,5-diol,1-phenyl-1H-imidazol-2,5-diol, 1H-imidazol-2,5-diol,1-methyl-1H-imidazol-2,5-diol, 1-phenyl-1H-imidazol-2,5-diol,1H-imidazol-2,5-diamine, 1-methyl-1H-imidazol-2,5-diamine,1-phenyl-1H-imidazol-2,5-diamine, 5-methoxy-1H-imidazole,5-methoxy-1-methyl-1H-imidazole, 5-methoxy-1-phenyl-1H-imidazole,2-methoxy-1H-imidazole, 2-methoxy-1-methyl-1H-imidazole,2-methoxy-1-phenyl-1H-imidazole, 2,5-dimethoxy-1H-imidazole,2,5-dimethoxy-1-methyl-1H-imidazole,2,5-dimethoxy-1-phenyl-1H-imidazole, 5-amino-1H-imidazol-4-carbonitrile,5-amino-1-methyl-1H-imidazol-4-carbonitrile,5-amino-1-phenyl-1H-imidazol-4-carbonitrile,5-hydroxy-1H-imidazol-4-carbonitrile,5-hydroxy-1-methyl-1H-imidazol-4-carbonitrile,5-hydroxy-1-phenyl-1H-imidazol-4-carbonitrile,2,5-dihydroxy-1H-imidazol-4-carbonitrile,2,5-dihydroxy-1-methyl-1H-imidazol-4-carbonitrile,2,5-dihydroxy-1-phenyl-1H-imidazol-4-carbonitrile,2,5-dimethoxy-1H-imidazol-4-carbonitrile,2,5-dimethoxy-1-methyl-1H-imidazol-4-carbonitrile,2,5-dimethoxy-1-phenyl-1H-imidazol-4-carbonitrile,4-chloro-1H-imidazol-5-ol, 4-chloro-1-methyl-1H-imidazol-5-ol,4-chloro-1-phenyl-1H-imidazol-5-ol, 4-chloro-1H-imidazol-2,5-diol,4-chloro-1-methyl-1H-imidazol-2,5-diol,4-chloro-1-phenyl-1H-imidazol-2,5-diol, 4-chloro-1H-imidazol-5-amine,4-chloro-1-methyl-1H-imidazol-5-amine,4-chloro-1-phenyl-1H-imidazol-5-amine, 4-chloro-1H-imidazol-2,5-diamine,4-chloro-1-methyl-1H-imidazol-2,5-diamine,4-chloro-1-phenyl-1H-imidazol-2,5-diamine,4-fluoro-1H-imidazol-2,5-diamine,4-fluoro-1-methyl-1H-imidazol-2,5-diamine,4-fluoro-1-phenyl-1H-imidazol-2,5-diamine,4-trifluoromethyl-1H-imidazol-2,5-diamine,1-methyl-4-trifluoromethyl-1H-imidazol-2,5-diamine,1-phenyl-4-trifluoromethyl-1H-imidazol-2,5-diamine,2-methyl-1H-imidazol-5-amine, 1,2-dimethyl-1H-imidazol-5-amine,2-methyl-1-phenyl-1H-imidazol-5-amine, 2-methyl-1H-imidazol-5-ol,1,2-dimethyl-1H-imidazol-5-ol, 2-methyl-1-phenyl-1H-imidazol-5-ol,1H-imidazol-2,4-diol, 1-methyl-1H-imidazol-2,4-diol,1-phenyl-1H-imidazol-2,4-diol, N-methyl-1H-imidazol-5-amine,N-ethyl-1H-imidazol-5-amine, 2-(1H-imidazol-5-ylamino)ethanol, and3-(1H-imidazol-5-ylamino)propane-1,2-diol.
 19. The composition of claim18 wherein said imidazoles are selected from the group consisting of1H-imidazol-2,5-diamine; 2-(5-Amino-1H-imidazol-2-ylamino)-ethanol;1H-imidazol-4,5-diamine; 1H-imidazol-2,4,5-triamine;4-amino-1H-imidazol-5-ol; 1H-imidazol-5-amine;2-methyl-1H-imidazol-5-ylamine; 1H-imidazol-2-amine;4-methyl-1H-imidazol-2-amine; 1H-imidazol-2,4-diamine; 1H-imidazol-5-ol;1H-imidazol-2,5-diol; and 1H-imidazol-2,4-diol.
 20. A keratin dyeingcomposition comprising: (A) a medium suitable for dyeing; and (B) one ormore 4H-[1,2,4]triazoles compounds selected from the group consisting of4H-[1,2,4]Triazole-3,5-diamine; N-Methyl-4H-[1,2,4]triazole-3,5-diamine;N-Methyl-4H-[1,2,4]triazole-3,5-diamine;N-Ethyl-4H-[1,2,4]triazole-3,5-diamine;N-Propyl-4H-[1,2,4]triazole-3,5-diamine;2-(5-Amino-4H-[1,2,4]triazol-3-ylamino)-ethanol;3-(5-Amino-4H-[1,2,4]triazol-3-ylamino)-propan-1-ol;3-(5-Amino-4H-[1,2,4]triazol-3-ylamino)-propane-1,2-diol;N-Phenyl-4H-[1,2,4]triazole-3,5-diamine;N-Thiophen-2-ylmethyl-4H-[1,2,4]triazole-3,5-diamine;N-Furan-2-ylmethyl-4H-[1,2,4]triazole-3,5-diamine;N-Benzyl-4H-[1,2,4]triazole-3,5-diamine;N,N-Dimethyl-4H-[1,2,4]triazole-3,5-diamine;N,N-Diethyl-4H-[1,2,4]triazole-3,5-diamine;5-Pyrrolidin-1-yl-4H-[1,2,4]triazol-3-ylamine;2-[(5-Amino-4H-[1,2,4]triazol-3-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(5-Amino-4H-[1,2,4]triazol-3-yl)-ethyl-amino]-ethanol; and5-amino-1H-[1,2,4]triazol-3-ol.
 21. A keratin dyeing compositioncomprising: (A) a medium suitable for dyeing; and (B) one or morefive-membered heteroaromatic keratin dyeing compounds with threeheteroatoms relating to the following compound:

 wherein R¹ and R⁴ are the same or different and are selected from thegroup consisting of: (a) C-linked monovalent substituents selected fromthe group consisting of: (i) substituted or unsubstituted, straight orbranched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl,aliphatic, heteroaliphatic, or heteroolefinic systems, (ii) substitutedor unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclicsystems, and (iii) substituted or unsubstituted, mono-, poly-, orper-fluoro alkyl systems; wherein said systems of (i), (ii) and (iii)comprise from about 1 to about 10 carbon atoms and from about 0 to about5 heteroatoms selected from the group consisting of O, S, N, P, and Si;(b) S-linked monovalent substituents selected from the group consistingof SA¹, SO₂A¹, SO₃A¹, SSA¹, SOA¹, SO₂NA¹A², SNA¹A², and SONA¹A²; (c)O-linked monovalent substituents selected from the group consisting ofOA¹, and ONA¹A²; (d) N-linked monovalent substituents selected from thegroup consisting of NA¹A², (NA¹A²A³)⁺, NA¹OA², NA¹SA², NO₂, N═NA¹,N═NOA¹, NA¹CN, NA¹NA²A³; (e) monovalent substituents selected from thegroup consisting of COOA¹, CONA¹ ₂, CONA¹COA², C(═NA¹)NA¹A², CN, and X;(f) fluoroalkyl monovalent substituents selected from the groupconsisting of mono-, poly-, and per-fluoro alkyl systems comprising fromabout 1 to about 12 carbon atoms and from about 0 to about 4heteroatoms; and (g) hydrogen wherein A¹, A², and A³ are monovalent andare independently selected from the group consisting of: H; substitutedor unsubstituted, straight or branched, alkyl, mono- or poly-unsaturatedalkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinicsystems; substituted or unsubstituted, mono- or poly-cyclic aliphatic,aryl, or heterocyclic systems; and substituted or unsubstituted, mono-,poly-, or per-fluoro alkyl systems; wherein said systems comprise fromabout 1 to about 10 carbon atoms and from about 0 to about 5 heteroatomsselected from the group consisting of O, S, N, P, and Si; wherein X is ahalogen selected from the group consisting of F, Cl, Br, and I.
 22. Thecomposition of claim 21 wherein said five-membered heteroaromatickeratin dyeing compounds are selected from the group consisting of[1,3,4]thiadiazole-2,5-diamine; N-Methyl-[1,3,4]thiadiazole-2,5-diamine;N-Ethyl-[1,3,4]thiadiazole-2,5-diamine;N-Propyl-[1,3,4]thiadiazole-2,5-diamine;2-(5-Amino-[1,3,4]thiadiazol-2-ylamino)-ethanol;3-(5-Amino-[1,3,4]thiadiazol-2-ylamino)-propan-1-ol;3-(5-Amino-[1,3,4]thiadiazol-2-ylamino)-propane-1,2-diol;N-Phenyl-[1,3,4]thiadiazole-2,5-diamine;N-Thiophen-2-ylmethyl-[1,3,4]thiadiazole-2,5-diamine;N-Furan-2-ylmethyl-[1,3,4]thiadiazole-2,5-diamine;N-Benzyl-[1,3,4]thiadiazole-2,5-diamine;N,N-Dimethyl-[1,3,4]thiadiazole-2,5-diamine;N,N-Diethyl-[1,3,4]thiadiazole-2,5-diamine;5-Pyrrolidin-1-yl-[1,3,4]thiadiazo-2-ylamine;2-[(5-Amino-[1,3,4]thiadiazol-2-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(5-Amino-[1,3,4]thiadiazol-2-yl)-ethyl-amino]-ethanol; and5-amino-[1,3,4]thiadiazol-2-ol.
 23. The composition of claim 21 whereinsaid five-membered heteroaromatic keratin dyeing compounds are selectedfrom the group consisting of [1,3,4]thiadiazole-2,5-diamine;N-ethyl-[1,3,4]thiadiazole-2,5-diamine; andN-phenyl-[1,3,4]thiadiazole-2,5-diamine.
 24. A keratin dyeingcomposition comprising: (A) a medium suitable for dyeing; and (B) one ormore five-membered heteroaromatic keratin dyeing compounds with threeheteroatoms relating to the following compound:

 wherein R¹ and R⁴ are the same or different and are selected from thegroup consisting of: (a) C-linked monovalent substituents selected fromthe group consisting of: (i) substituted or unsubstituted, straight orbranched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl,aliphatic, heteroaliphatic, or heteroolefinic systems, (ii) substitutedor unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclicsystems, and (iii) substituted or unsubstituted, mono-, poly-, orper-fluoro alkyl systems; wherein said systems of (i), (ii) and (iii)comprise from about 1 to about 10 carbon atoms and from about 0 to about5 heteroatoms selected from the group consisting of O, S, N, P, and Si;(b) S-linked monovalent substituents selected from the group consistingof SA¹, SO₂A¹, SO₃A¹, SSA¹, SOA¹, SO₂NA¹A², SNA¹A², and SONA¹A²; (c)O-linked monovalent substituents selected from the group consisting ofOA¹, and ONA¹A²; (d) N-linked monovalent substituents selected from thegroup consisting of NA¹A², (NA¹A²A³)⁺, NA¹OA², NA¹SA², NO₂, N═NA¹,N═NOA¹, NA¹CN, NA¹NA²A³; (e) monovalent substituents selected from thegroup consisting of COOA¹, CONA¹ ₂, CONA¹COA², C(═NA¹)NA¹A², CN, and X;(f) fluoroalkyl monovalent substituents selected from the groupconsisting of mono-, poly-, and per-fluoro alkyl systems comprising fromabout 1 to about 12 carbon atoms and from about 0 to about 4heteroatoms; and (g) hydrogen wherein A¹, A², and A³ are monovalent andare independently selected from the group consisting of: H; substitutedor unsubstituted, straight or branched, alkyl, mono- or poly-unsaturatedalkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinicsystems; substituted or unsubstituted, mono- or poly-cyclic aliphatic,aryl, or heterocyclic systems; and substituted or unsubstituted, mono-,poly-, or per-fluoro alkyl systems; wherein said systems comprise fromabout 1 to about 10 carbon atoms and from about 0 to about 5 heteroatomsselected from the group consisting of O, S, N, P, and Si; wherein X is ahalogen selected from the group consisting of F, Cl, Br, and I.
 25. Thecomposition of claim 24 wherein said five-membered heteroaromatickeratin dyeing compounds are selected from the group consisting of[1,3,4]oxadiazole-2,5-diamine; N-Methyl-[1,3,4]oxadiazole-2,5-diamine;N-Ethyl-[1,3,4]oxadiazole-2,5-diamine;N-Propyl-[1,3,4]oxadiazole-2,5-diamine;2-(5-Amino-[1,3,4]oxadiazol-2-ylamino)-ethanol;3-(5-Amino-[1,3,4]oxadiazol-2-ylamino)-propan-1-ol;3-(5-Amino-[1,3,4]oxadiazol-2-ylamino)-propane-1,2-diol;N-Phenyl-[1,3,4]oxadiazole-2,5-diamine;N-Thiophen-2-ylmethyl-[1,3,4]oxadiazole-2,5-diamine;N-Furan-2-ylmethyl-[1,3,4]oxadiazole-2,5-diamine;N-Benzyl-[1,3,4]oxadiazole-2,5-diamine;N,N-Dimethyl-[1,3,4]oxadiazole-2,5-diamine;N,N-Diethyl-[1,3,4]oxadiazole-2,5-diamine;5-Pyrrolidin-1-yl-[1,3,4]oxadiazol-2-ylamine;2-[(5-Amino-[1,3,4]oxadiazol-2-yl)-(2-hydroxy-ethyl)-amino]-ethanol;2-[(5-Amino-[1,3,4]oxadiazol-2-yl)-ethyl-amino]-ethanol; and5-amino-[1,3,4]oxadiazol-2-ol.
 26. A keratin dyeing compositioncomprising: (A) a medium suitable for dyeing; and (B) one or morefive-membered heteroaromatic keratin dyeing compounds with threeheteroatoms relating to the following compound:

 wherein R² and R³ are the same or different and are selected from thegroup consisting of: (a) C-linked monovalent substituents selected fromthe group consisting of: (i) substituted or unsubstituted, straight orbranched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl,aliphatic, heteroaliphatic, or heteroolefinic systems, (ii) substitutedor unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclicsystems, and (iii) substituted or unsubstituted, mono-, poly-, orper-fluoro alkyl systems; wherein said systems of (i), (ii) and (iii)comprise from about 1 to about 10 carbon atoms and from about 0 to about5 heteroatoms selected from the group consisting of O, S, N, P, and Si;(b) S-linked monovalent substituents selected from the group consistingof SA¹, SO₂A¹, SO₃A¹, SSA¹, SOA¹, SO₂NA¹A², SNA¹A², and SONA¹A²; (c)O-linked monovalent substituents selected from the group consisting ofOA¹, and ONA¹A²; (d) N-linked monovalent substituents selected from thegroup consisting of NA¹A², (NA¹A²A³)⁺, NA¹OA², NA¹SA², NO₂, N═NA¹,N═NOA¹, NA¹CN, NA¹NA²A³; (e) monovalent substituents selected from thegroup consisting of COOA¹, CONA¹ ₂, CONA¹COA², C(═NA¹)NA¹A², CN, and X;(f) fluoroalkyl monovalent substituents selected from the groupconsisting of mono-, poly-, and per-fluoro alkyl systems comprising fromabout 1 to about 12 carbon atoms and from about 0 to about 4heteroatoms; and (g) hydrogen wherein A¹, A², and A³ are monovalent andare independently selected from the group consisting of: H; substitutedor unsubstituted, straight or branched, alkyl, mono- or poly-unsaturatedalkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinicsystems; substituted or unsubstituted, mono- or poly-cyclic aliphatic,aryl, or heterocyclic systems; and substituted or unsubstituted, mono-,poly-, or per-fluoro alkyl systems; wherein said systems comprise fromabout 1 to about 10 carbon atoms and from about 0 to about 5 heteroatomsselected from the group consisting of O, S, N, P, and Si; wherein X is ahalogen selected from the group consisting of F, Cl, Br, and I.
 27. Thecomposition of claim 26 wherein said five-membered heteroaromatickeratin dyeing compounds are selected from the group consisting of[1,2,5]Thiadiazole-3,4-diamine; 4-Amino-[1,2,5]thiadiazol-3-ol;N-Methyl-[1,2,5]thiadiazole-3,4-diamine;N-Ethyl-[1,2,5]thiadiazole-3,4-diamine;2-(4-Amino-[1,2,5]thiadiazol-3-ylamino)-ethanol;2-[4-(2-Hydroxy-ethylamino)-[1,2,5]thiadiazol-3-ylamino]-ethanol; and5-amino-[1,3,4]thiadiazol-2-ol.
 28. The composition of claim 26 whereinsaid five-membered heteroaromatic keratin dyeing compounds are selectedfrom the group consisting of [1,2,5]thiadiazole-3,4-diamine.
 29. Akeratin dyeing composition comprising: (A) a medium suitable for dyeing;and (B) one or more five-membered heteroaromatic keratin dyeingcompounds with one, two, or three heteroatoms relating to the followingcompound:

 wherein Z is selected from the group consisting of S and O;  wherein Yis selected from the group consisting of NA¹, S and O;  wherein R¹, R²,R³, and R⁴ are the same or different and are selected from the groupconsisting of: (a) C-linked monovalent substituents selected from thegroup consisting of: (i) substituted or unsubstituted, straight orbranched, alkyl, mono- or poly-unsaturated alkyl, heteroalkyl,aliphatic, heteroaliphatic, or heteroolefinic systems, (ii) substitutedor unsubstituted, mono- or poly-cyclic aliphatic, aryl, or heterocyclicsystems, and (iii) substituted or unsubstituted, mono-, poly-, orper-fluoro alkyl systems; wherein said systems of (i), (ii) and (iii)comprise from about 1 to about 10 carbon atoms and from about 0 to about5 heteroatoms selected from the group consisting of O, S, N, P, and Si;(b) S-linked monovalent substituents selected from the group consistingof SA¹, SO₂A¹, SO₃A¹, SSA¹, SOA¹, SO₂NA¹A², SNA¹A², and SONA¹A²; (c)O-linked monovalent substituents selected from the group consisting ofOA¹, and ONA¹A²; (d) N-linked monovalent substituents selected from thegroup consisting of NA¹A², (NA¹A²A³)⁺, NA¹OA², NA¹SA², NO₂, N═NA¹,N═NOA¹, NA¹CN, NA¹NA²A³; (e) monovalent substituents selected from thegroup consisting of COOA¹, CONA¹ ₂, CONA¹COA², C(═NA¹)NA¹A², CN, and X;(f) fluoroalkyl monovalent substituents selected from the groupconsisting of mono-, poly-, and per-fluoro alkyl systems comprising fromabout 1 to about 12 carbon atoms and from about 0 to about 4heteroatoms; and (g) hydrogen wherein A¹, A², and A³ are monovalent andare independently selected from the group consisting of: H; substitutedor unsubstituted, straight or branched, alkyl, mono- or poly-unsaturatedalkyl, heteroalkyl, aliphatic, heteroaliphatic, or heteroolefinicsystems; substituted or unsubstituted, mono- or poly-cyclic aliphatic,aryl, or heterocyclic systems; and substituted or unsubstituted, mono-,poly-, or per-fluoro alkyl systems; wherein said systems comprise fromabout 1 to about 10 carbon atoms and from about 0 to about 5 heteroatomsselected from the group consisting of O, S, N, P, and Si; wherein X is ahalogen selected from the group consisting of F, Cl, Br, and I; and (c)at least one five-membered ring developer selected from the groupconsisting of thiophenes, pyrroles, furans, pyrazoles, imidazoles,thiazoles, oxazoles, isothiazoles, and isoxazoles.
 30. The compositionof claim 29 wherein said five-membered ring developer is a pyrazole. 31.The compositions of claim 30 wherein said five-membered ring developeris selected from the group consisting of1-methyl-1H-pyrazole-4,5-diamine,2-(4,5-diamino-1H-pyrazol-1-yl)ethanol,1-isopropyl-1H-pyrazole-4,5-diamine,1-(4-methylbenzyl)-1H-pyrazole-4,5-diamine,1-(benzyl)-1H-pyrazole-4,5-diamine,1-(4-chlorobenzyl)-1H-pyrazole-4,5-diamine, and1-Hydroxyethyl-4,5-diaminopyrazole sulphate.
 32. The composition ofclaim 31 wherein said five-membered ring developer is selected from thegroup consisting of 1-methyl-1H-pyrazole-4,5-diamine;1-Hydroxyethyl-4,5-diaminopyrazole sulphate; and2-(4,5-diamino-1H-pyrazol-1-yl)ethanol.